Author Archive for Kristen Webb Wright

How Journaling Is Transforming My Career

It’s no secret that I believe in the transformative power of journaling. But I’ll admit: I’ve tended to segment my professional life out of my journals, keeping them mainly as a space for personal reflection and exploration.

Six months ago, I was honored to step into the role of Interim Marketing Director for Day One Journal. This time not only deepened my commitment to journaling, but also reshaped my approach to it. I discovered how my journal transformed into a crucial tool for managing anxieties, anchoring my daily routine, and sharpening my focus.

My journal, once a simple refuge for thoughts and memories, became a strategic asset, helping me navigate the complexities of leadership and enhancing my productivity in a way I hadn’t anticipated.

Beyond Freewriting: Embracing Structure in My Journal

In the past, my journaling method has been predominantly freewriting—usually about the events of my day, what I hoped to remember. This method of journaling provides a certain freedom and creative expression, but also has its limitations.

Specifically, my past journals rarely touch on the multifaceted challenges of my work life. Freewriting is satisfying for personal exploration, but I wasn’t leveraging journaling’s potential to enhance my effectiveness at work or tackle the nuanced challenges I face in my career.

After interviewing many Day One power users, some of whom have maintained daily journaling streaks spanning years, a common thread emerged: structured journaling. These users didn’t just journal; they did so with precision, using tailored questions and prompts.

This insight inspired me to rethink my own approach to journaling. Was I really getting the most from only freewriting in my journal?

My time as an interim lead provided me with a fresh start, a chance to try a more structured and strategic journaling approach. And by adopting a template-driven method, I began to ask myself the same pivotal questions each day, systematically addressing key aspects of my personal growth and professional development.

What I’ve Learned Through Structured Journaling

Each morning, before the rush of tasks and meetings, I spend time with my journal. I block a full hour off in my calendar, granting myself that time as a non-negotiable commitment to reflection and planning.

I’ll admit—I was nervous about dedicating such a significant portion of my morning to journaling, especially when there were countless other pressing tasks awaiting my attention. Yet, this practice soon proved essential. This hour of journaling has become less about the time spent and more about investing in clarity, purpose, and preparation.

Journaling not only sets the tone for my day, grounding me and sharpening my focus, but also helps me identify and prioritize the tasks that will have the most impact. Through my structured journaling journey, I’ve gained invaluable insights that go beyond simple task management.

Here’s what I learned:

  • Understanding My Mental Landscape: Journaling helped me understand that my initial apprehension about spending time on it was rooted in a common professional pitfall—overvaluing immediate action over thoughtful preparation. The time spent journaling turned out to be one of the most productive parts of my day, giving me clarity and a much-needed pause to sort my thoughts.
  • Focused Clarity: Structured journaling allowed me to zero in on what was truly important each day. Instead of scattering my thoughts, the template guided me to focus on specific areas such as daily priorities, emotional states, and anxieties, leading to clearer decision-making.
  • Navigating Anxiety with Action: I discovered that my anxieties and fears often blocked my productivity. By identifying specific anxieties each morning, journaling allowed me to turn these into actionable steps. This not only cleared mental roadblocks but also propelled me forward, maintaining my momentum throughout the day.
  • Deeper Insight into Personal Patterns: Using a structured format revealed consistent themes and recurring challenges in both my personal and professional life. This insight allowed me to address underlying issues rather than just the symptoms.

Through these lessons, I realized that journaling is much more than a personal tool—it’s a compass that guides me through the complexities of daily responsibilities and personal growth.

Sharing the Journal Template That Has Guided Me

My new morning journal template has evolved into a tool that encompasses both my professional responsibilities and personal wellness, guiding me through each day with intentionality and reflection. Here are the key sections:

Daily Structure:

  • Date & Freewrite: I still begin my journaling with a brief freewriting session to clear my mind and capture any immediate thoughts. I then copy/paste this freewriting portion into my separate “non-work” journal.
  • Key Tasks: I list all my tasks for the day and format them in a checklist format. I also make a list of tasks for things I need to respond to across platforms we use at Automattic (like P2, Slack, and email).
  • Time Blocking: I schedule out my day, assigning time for each of the tasks on my to-do list. I also schedule in breaks and workouts, because I also want to prioritize these. Time-blocking is always enlightening, reminding me what I can actually accomplish in the time I have each day.

Reflective Inquiries:

  • Physical and Emotional Check-In: I try to assess my physical and emotional states.
  • Focused Reflections: I explore any feelings of anxiety, nervousness, uncertainty, and fear. I then go a bit deeper, attempting to identify their roots and reframing them as opportunities for action.
  • Gratitude and Connections: I note good things that have happened that are usually small details of the day before. I also jot down a few things I’m thankful for and people who are on my mind.
  • Meal and Fitness Planning: I decide what I’ll eat and then what type of workout I want to do that day.

Personal Growth Pathways:

  • Pathways to Growth: These points focus on areas of growth I’ve wanted to remain mindful of on a daily basis, such as embracing vulnerability, cultivating emotional awareness, exploring creativity, and balancing solitude with social interactions.

Additional Sections:

  • Affirmations, Links, and Ideas: Finally, I include sections for daily affirmations, useful links, and any random ideas for the day.

Download My Journal Template for Day One

My hope is that this journal template isn’t just a planner; it’s a holistic tool that helps bridge the gap between personal introspection and professional demands. I also hope it provides a jumpstart for creating your own personal journal template (it’s totally customizable!)

You can download my journal template here. (This link will let you make a new entry in your own Day One journal starting with the content of my daily template. Then copy/paste this entry into a new template.)

A Few Tips for Implementing Structured Journaling Into Your Daily Routine

Finally, here are some things I’ve learned about how to add a structured journaling practice into your daily routine:

  1. Start Small: I know setting aside a full hour for journaling may seem like a big commitment. Some days, especially when time is tight, I’ve found that even 15-20 minutes can be sufficient to gather thoughts and set the tone for the day. The key to seeing the benefits of journaling is consistency, not duration. Feel free to start with a manageable timeframe that fits into your schedule.
  2. Schedule Your Sessions: Treat your journaling time like any important appointment. Block it off in your calendar to establish a routine, ensuring you have dedicated time set aside each day. As I learned, by blocking out time on your calendar, you’re more likely to commit and stick to the habit.
  3. Customize Questions and Sections of Your Template: My journal template has evolved quite a bit over the last six months. I’ve added some new sections and questions, and dropped others that just didn’t work. Feel free to tailor your journal template to make it truly yours.
  4. Embrace Flexibility: If certain questions don’t resonate on a given day, feel free to skip them. Journaling should be a stress-relieving activity, not another source of pressure.
  5. Give Yourself a Reward: Inspired by James Clear’s Atomic Habits, make your journaling time enjoyable. Pair journaling with a favorite morning ritual, like a cup of coffee or a soothing candle, or … a relaxing neck wrap. Reward yourself either while you journal or just after you finish can help you build positive associations with the activity.
  6. Utilize Day One’s Features: Leverage the customizable features of Day One by setting up a personalized journaling reminder that automatically loads your template at your designated journaling time. Then, all you have to do is click the notification to start writing.
  7. Partner with ChatGPT: I was skeptical at first, but I’ve been surprised at how ChatGPT is a great companion to journaling. It can offer daily affirmations, help brainstorm solutions when you’re stuck, and assist in unpacking complex emotions. I’ve often been surprised by the new insights and perspectives I gained with a quick chat.

Wrapping Up

The last six months have not only reshaped my approach to journaling but have also underscored its value as a personal growth and productivity tool. The practice of journaling has emerged as a cornerstone of my daily life, deeply influencing how I perceive and interact with the world around me. It has equipped me with the tools to be more reflective, resilient, and resourceful. Journaling has taught me that the act of writing can be as powerful as any other business strategy or leadership tactic—if not more so because it starts with leading oneself.

Interested in seeing what structured journaling can do for your day-to-day productivity and personal insight? Feel free to download my journal template here.


About Kristen

Kristen Webb Wright is the author of three books on journaling. With a passion for writing and self-reflection, Kristen uses her experience with journaling to help others discover the benefits of documenting their thoughts, feelings, and experiences. In her role at Day One, she helps to promote the power of journaling so people from all walks of life can experience the transformative power of journaling.

My New Book, The Transformation Year, is Here

Outside my office window, the December morning sky is pale gray. A cardinal lands on a branch of the redbud tree, then quickly flies away. The trees are bare now, although some of the last deciduous holdouts in the neighborhood are just peaking with their fall colors. One particular tree, down the street, was bright red just nine days ago, and I was astonished to find it transformed yesterday morning, with all its leaves dropped in piles around it on the ground.

Keeping a journal has helped me pay attention to these things—the sky, the trees, urban wildlife, and how the seasons change. Keeping a record of my life has also taught me to document my own interior landscapes, helping me untangle the threads of what has changed over the years—and what remains the same.

I believe keeping a journal is one of the most important projects we can undertake during our lives, yet the task is rarely regarded with wonder. I personally know the toil it can sometimes involve—an exhausted mind and heart would rather do anything but find a blank page to fill. 

The past few years have brought unexpected changes to my life: a difficult pregnancy, the challenges of being a new parent, a pandemic, losing my dad suddenly to a heart attack. These big life events have shown me that the mental, physical, and emotional task of keeping a record of a life will indeed have gaps and silences; as much as I was convinced that keeping a journal should be a necessary daily task much like eating, sleeping, or even exercise, sometimes, frankly, you don’t want to write about anything at all.

My journal has been my mirror and compass, reflecting my true self back to me, and giving me a sense of direction I would not have known otherwise.

On the other hand, keeping a journal has given me a profound sense of meaning in my life, which is why I know it’s my duty for a lifetime. My journal has been my mirror and compass, reflecting my true self back to me, and giving me a sense of direction I would not have known otherwise. I am often surprised when I look back at my journals only to discover memories that I might have otherwise forgotten—moments of contentment, awe, and sheer joy. Most of all, keeping a journal has taught me that each day holds something significant, something worth recording. Keeping a journal has reminded me again and again of the richness and abundance of my daily life, no matter how mundane or predictable some days may seem.

Journaling has meant so much to me, I somehow managed to publish two books of my journals; I’ve taught workshops and webinars on journaling; and now, to my astonishment, my career has shifted so that I can focus on helping others discover the benefits of journaling full-time. Many of my friends and family know how passionate I am about journaling, so I often get asked how to get started. I appreciate the genuine interest people show in wanting to keep a journal, but they sometimes seem defeated before they even begin. Maybe the commitment seems too large, too looming. Everyone is so busy these days, who really has the time? Where do you begin? How do you develop a daily journaling habit that lasts? And what exactly do you write about? (Not to mention—something I realized I skimmed over once, assuming everyone already knows—what is journaling, really, anyway?)

My simple definition of journaling is this: Journaling is a personal record of experiences, events, insights, and reflections, kept on a regular basis.

My simple definition of journaling is this: Journaling is a personal record of experiences, events, insights, and reflections, kept on a regular basis. You don’t have to journal every day, but some people may find it helpful or beneficial to do so, as I have. Starting a journal can be as easy as opening a blank document on your computer, grabbing a pen and a notebook, using a journaling app like Day One, or even recording yourself in a video or audio message on your phone. There are many ways to keep a journal, but the most important thing is to keep it simple and easy.

As for deciding what to write about, journal prompts can be a great way to get started. Journaling prompts are questions or ideas that can help you to get into the right frame of mind to begin thinking and writing. Although I don’t usually use journaling prompts myself, I realized that creating prompts is one of the best ways that I can help people start, maintain, and actually enjoy a journaling practice. 

The Transformation Year is designed to be your guide through a life-changing year of journaling—and self-discovery.

The Transformation Year is designed to be your guide through a life-changing year of journaling—and self-discovery. It’s also the book that I needed, as it became a way to compile all the life-changing quotes I’ve collected over the years. As I’ve written this book, I’ve often caught myself wanting to answer the prompts in my own writing, too. In addition to the quotes, each day includes a prompt to help you express yourself and learn more about yourself, another prompt to help you appreciate what you are grateful for, and a simple mindfulness exercise to bring you into the present moment. 

You can start The Transformation Year at any time of the year, on any day of the week. The entries are numbered by day, not by date, so you can take a break at any time and start again where you left off. All you need is a bookmark to mark your place as you progress through the year.

The theme of this book, of course, is transformation. Journaling is one of those rare endeavors that can bring a profound change to you and your life, as you explore your experiences and memories, and express your thoughts and emotions. But like most meaningful endeavors, journal-keeping does require some effort and commitment. My hope is that The Transformation Year will make you excited to meet each new day with new discoveries, ideas, and insights—so that keeping a journal can even be fun. 

Most of all, I hope this book will help you see your daily life in a new way, and that it will inspire you to develop a journaling habit that brings as much meaning, satisfaction, and transformation as I have experienced in mine.

Here’s to the next year, brimming with possibilities—and all the treasures it will surely bring. Journal-keeping offers a rare type of alchemy, a transformation that’s uniquely your own.

kristen

Many people supported and loved me through my own Transformation Year. I am overwhelmed with love and gratitude for the people who have encouraged me and enriched my life.

My special thanks and love go to:

My husband, Jacob—you always let me be who I am. I love you, and I am so grateful to have found a life partner and friend in you. I love the life we are building together every day.

My son, Hugh—you are too young to read this, but I hope to instill the same love of reading and writing that has sustained and changed me. You brighten my day, and I love seeing the world through your eyes.

My mom, Janet Webb—your strength has shown me how to forge a new path in life. You remind me how determination makes all things possible. I love you.

Cory and Lindsey Miller—The Transformation Year simply would not have happened without you. Thank you for believing in my dream and investing in it through AllCounseling.com.

My siblings and their families: Shelby, Justin, Amelia, and Chloe Perry; Andrew, Christen, and Graham Webb—I love you all so much. I am thankful for each of you and your uniqueness.

My in-laws, Mark and Pat Wright—thanks for your support and for helping me with Hugh so I could have the time I needed to work on this book. You are both such a blessing to me.

My grandma, Evelyn McConnell: thank you for reading my books and teaching me the values of warmth and generosity.

My best friend, Emily Trotter—I owe the title of this book, The Transformation Year, completely to you. Thank you for always reminding me to laugh. You have been there for me in countless ways that I will never forget, and your friendship is one of the great gifts of my life.

My best friend, Rebecca Dellinger—so much of this book is the culmination of our conversations and adventures together. I love you dearly.

The amazing women whose friendship, support, and guidance have made a difference in my life and my work: Vicky Hampton, Kelly Gallagher, Joyce McConnell, Marcia Morris, Patti Ream, Kathy Zant, Sarah Ulmer, Elise Alley, and Julie Marks Blackstone.

Finally, to my dad, Andy Webb—I miss you every single day. Losing you has been the most difficult thing I have ever endured, but you have given me the gift of realizing how much each day counts.

Farewell, iThemes + The Journey Ahead

Not all big transitions in life have a ceremony or a big event to mark the occasion, but I know the importance of acknowledging the end of an era. As my chapter with iThemes draws to a close next week, I wanted to share a bit about what I’ve learned, what the journey has meant, and where I’m heading next.

My time at iThemes has represented eleven full years of my life: building meaningful relationships and friendships; professional and personal growth; developing my instincts for business; embracing the challenges of loss, change, and even success. 

Early into my first year at iThemes, we had our team motto created in giant letters to hang in the lobby of the office. I stood back, took photos, and watched as the letters were leveled and attached to the wall. Every day we walked through the front doors to work, we’d be reminded: 

Make People’s Lives Awesome. 

For us, this motto meant a responsibility to three sets of people, in this order: 

  • Our families
  • Our fellow team members
  • Our customers 

iThemes was always, for me, a place to connect to that mission. I knew the work I was doing mattered because it was fueled by a shared purpose. Whatever we were doing to innovate and serve our customers, we also wanted to make an awesome life for the people closest to us—and for ourselves. 

But the truth is, I always struggled a bit with how to define myself in terms of my career. iThemes has represented so such much to me, but I’ve always had other interests. Behind the scenes, late at night, and on the weekends, I was doing other work. I just had no idea how to integrate it all—the “iThemes” me, and the real me, the writer, the journal-keeper. 


This quote has followed me around for years, showing up again and again in unexpected ways and places:  

“What you seek is seeking you.”
– Rumi 

These words speak to two parts of me: the one that’s optimistic and hopeful, then the other one that dabbles in pure skepticism and cynicism. I’m mostly suspicious of the mystical, but I wanted this to be true: could what I want also want me? Is it possible there’s a mutual searching between us and what we long for? 

In 2014, I started keeping a daily journal. Introduced to mindfulness by my counselor, I discovered this novel approach to focusing my attention on the present moment. Mindfulness helped me discover a new truth that will guide me for the rest of my life:

Our days are full of meaning and significance if we’re paying attention. 

Keeping a journal was a natural outpouring of shifting my awareness to the present: with so much beauty, with so much meaning and significance, I wanted to capture it all, keep a record. A day’s events began to feel so important to me, I couldn’t let them slip away without wanting to capture all the details. Maybe it was a duty I felt to tend to the new outlook on life that I had been given. 

Ultimately, in keeping a journal, I learned I want to be a writer. My job at iThemes has always relied heavily on technical writing, copywriting, and SEO. On the side, I began to dabble in poetry and flash non-fiction, in short stories, and even outlined a novel or two. But I know, deep down, my defining genre is memoir—specifically, in the form of keeping a journal. 

But how can you possibly make a living keeping a journal? That was the perplexing question that seemed to only have one answer: you can’t.

But something within me was defiant. I was going to stick with it no matter what. Sometimes, I was even bewildered at my commitment to the work: thousands of hours, two books, an email series, teaching workshops, retreats, and recently, a webinar. All on the subject of journaling. That’s how much it meant to me. That’s how much I needed it.

Then earlier this summer, I happened on a job posting. And I almost fell out of my chair. I knew, instantly, that I had found my dream job. So I spent the next 48 hours working on my resume (which was nonexistent), then applying. I didn’t mention it to anyone. 

The next week, I went to Colorado with my family on vacation. I checked my email daily for updates. The days went on, the job posting went down, and I began to think the opportunity had passed. I was on a hike by myself, cresting a ridge to a view of Pikes Peak, when the quote struck me again. Except for this time, I felt an odd sense of assurance. Something seemed to tell me that all the work I’ve done over the years has meant something. It hadn’t all been wasted.

Back at home, I did some digging. I contacted a friend who I thought might know something about the role. She did, and with an astounding amount of kindness, she flagged my resume. The next few weeks were a whirlwind, but I dug in and gave it all my effort. I sat at stoplights, whispering to myself, “I want this job.” Like saying it out loud meant it wasn’t just locked up in my head and heart. I succumbed, at times, to more angst than I’d like to admit, but tried to stay hopeful, and vulnerable to how much I wanted it. 

So today I’m excited to finally share … 

I’m the new Digital Marketing Manager for the Day One journaling app. If dream jobs exist, this is mine: helping others learn how to keep a journal, and with the best tool built exclusively for that purpose, Day One. 

On Keeping a Journal

We all have an impulse to document our lives in one way or another: through the photos in our camera roll, through Facebook posts, tweets, or Instagram reels. Maybe it’s through to-do lists or calendar invites or blog posts. Some of this we do plainly in public view, so we may carefully curate what other people see about our lives. 

A journal is simply a personal record of experiences, occurrences, insights, and reflections kept on a regular basis.

A journal is simply a personal record of experiences, occurrences, insights, and reflections kept on a regular basis. A journal, however, is the antithesis of what we may share in public.

A journal is the private, sacred space we all need to process thoughts, record memories, and make sense of our lives. No one in the world is watching. Not your cousin or your coworkers or big tech. With a journal, you trade in the affirmation you get in the form of likes or hearts or retweets, but the work you do to face a blank page with honesty will keep you true to yourself. 

A journal will help you remember your life, stand witness to it, and capture time as it passes. My journal is full of memories, some that might have been otherwise forgotten. On countless occasions, I’ve experienced the strange phenomenon of a memory being unearthed just by reading a journal entry. Would I have remembered it otherwise? I’m not so sure.

A journal is both a mirror and a compass, and I believe it’s one of the most important practices we can develop to foster reflection, introspection, and clarity. I’ve learned the sound of my own voice, and the two different stories I often tell myself (my memory and my journal often offer two very different narratives).

Keeping a journal will teach you to see all the beauty and wonder and significance in your life. It’s there, I promise. 

So, let me say this: 

Find your passion. Figure out what you truly want in life. Be brave enough to grant yourself the freedom to really, really want something. 

Find your passion. Figure out what you truly want in life. Be brave enough to grant yourself the freedom to really, really want something. 

All of it matters. All the work you’re doing now, even if it seems disjointed from who you wish you were or what you wish you could be doing.

Reframe this struggle as the primary indicator of how meaningful and important it is to you. After all, good stories are about two things: 1) wanting something and then 2) overcoming the inevitable obstacles you’ll face to get there. 

Cultivate your sense of identity, even if it means you secretly rebel against what you ought to be doing. Don’t give up. All roads will lead you there. But you must stay on the road.

So, what would happen if this was true for you? 

What you seek is, indeed, seeking you. 


I owe iThemes and the amazing people there a debt of gratitude: for believing in me, for trusting me, for giving me a place to grow, and for letting me be who I truly am.

As this chapter in my life draws to a close, just know it’s been one of the most rewarding and meaningful things I’ve ever done—getting to work with you all, help build this business, solve problems together, and serve our customers. We’ve had a ton of fun, and those stories are the ones I’ll always hold dear. I’ll miss you all immensely. 

This song by one of my favorite artists says it best:

Love is change.

With much love, and much hope, for the journey ahead.

kristen

Introducing The Transformation Year, A Daily Journaling Prompt Sent to Your Inbox

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s you know, I’m pretty passionate about journaling. So much so, I published two books of my journals. I often get asked how to get started journaling and what to write about, so I’m proud to introduce The Transformation Year, a new year-long email series with a daily journaling prompt.

The science is clear. Journaling offers a host of benefits.

According to mental health professionals, journaling is one of the most recommended tools to have a clearer mind and a happier life. Journaling has been proven to provide all these benefits and more:

  • Reduce anxiety and stress
  • Regulate emotions
  • Strengthen memory
  • Solve problems more efficiently
  • Increase self-awareness
  • Speed up physical healing
  • Boost happiness & positivity
  • Find more inspiration and be more creative
  • Become more mindful
  • Gain self-confidence
  • Set and achieve goals
  • Track progress and growth

But what do I write about?

The problem most people have when it comes to journaling is knowing what to write about. Starting at a blank page or screen can be so overwhelming, you may not know where to begin.

The key to a successful journaling practice is making the question of “what do I write about?” as simple to answer as possible.

You can do that in a number of ways:

  • Through journaling prompts – Journaling prompts offer a great starting point by asking questions to help you get writing.
  • Getting into a mindset for introspection and reflection – Our “everyday” operating minds may need to switch into a different gear to journal. Having a specific place, time of day, or ritual that helps get you into “writing mode” may help.
  • Developing your own unique approach to journaling – Journaling is an avenue of self-expression that has no rules or guidelines. Write, draw, add photos–just capture whatever is on your mind.

Over the past eight years, I know both the reward and challenges of keeping a journal. If there’s one thing I’ve learned, it’s that having a daily reminder that inspires and encourages journaling is key to success.

The Transformation Year Will Help You Keep a Journal

The Transformation Year is a year-long email series with daily journal prompts to guide you through the two proven types of journaling, along with inspirational quotes and an emphasis on being mindful throughout your day.

The Transformation year is designed to help you know what to write about, offering you a choice of several prompts:

  • An inspirational quote to help you get in a thoughtful, reflective mindset.
  • Expressive writing topics to help you express what’s on your and in your heart
  • Gratitude focus questions to help you become more aware of all the good things in your life each day
  • Mindful reflection exercises to help you anchor to the present and be more aware of your day as it unfolds.

Why I Developed The Transformation Year

Ultimately, The Transformation Year is the resource I still need. Toni Morrison said, “Write the book you want to read,” and I took that to heart.

I wanted to distill everything I’ve learned about journaling on a daily basis into something I could use personally. But knowing that it might benefit others, too, has given me the determination and resolve I’ve needed to finally get it written.

What If You Kept a Journal for a Year?

How might keeping a journal change your life? With all the proven benefits of journaling, which ones do you need the most?

The Transformation Year is designed so that you can begin anytime, on any date. So sign up for the daily email today. I truly hope it will be a transformative resource as you start or continue your journaling practice.

10 Things I Learned in 10 Years of Selling WordPress Products

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his week, I wrap up nearly a decade at iThemes. I didn’t want to let this transition go by without reflecting on what I learned, celebrating some achievements, and expressing gratitude to the awesome team that became a second family to me. You don’t spend 10 years together without having some stories to tell. 

If I’m honest, I never saw myself in marketing or even business. I studied art in college, assuming I would go on to a career in the humanities or education. Once I left college, I’ll admit I floated from one non-profit job to another, not sure where I belonged. But that’s when the special place of iThemes welcomed me, introducing me to the wonderful world of WordPress. 

It’s been said that WordPress is a movement, a philosophy. The open-source initiative means freedom: ideas are shared; collaboration is key; transparency is necessary. Like all idealistic notions, of course, nothing is perfect. But I was drawn to these high ideals of empowerment and free expression; I could get behind these values as the foundation of our business. 

What I quickly learned, though, is that WordPress also represents an entire thriving business ecosystem. Talented teams around the globe work every day to bring innovative tools that build on the foundation of WordPress. The WordPress marketplace faces both some unique and universal business challenges. Ask any developer turned overnight CEO; any former art student turned content marketer. 

I gave myself the challenge of distilling down my experience of selling and marketing WordPress products as a way to look back and also a way to look forward. I believe these lessons will continue to be true long into the future. So, here goes.

1. Marketing … with Heart 💛 

Let’s face it: marketing can get a bad wrap. If there was one thing I realized during my first few months at iThemes, it was the challenge of building a marketing approach that was also a bridge between our customers and the rest of the team. 

What I learned was the importance of what I call marketing with heart. It’s an approach to marketing that is built on a few key values:

  • Be helpful.
  • Be generous.
  • Be sincere, authentic, and honest. 
  • Be clear and concise. 
  • Respect your customers’ time (as well as their inbox and timeline)
  • Earn respect with your team. 
  • Commit to excellence. No shortcuts.
  • Do the right thing. 
  • Make people’s lives awesome

With any marketing campaign, I learned to ask myself:

  • How are we being helpful and generous?
  • What’s confusing about this?
  • What exactly am I asking the customer to do?
  • How can I make this action easier for the customer? 
  • Is there anything I’m being lazy about?
  • How can we surprise and delight anyone who reads or sees this?

Of course, all marketing comes with one primary goal: make more money. But I’m here to say you can make money and hold these priorities at the same time.

2. Sell The Thing You Made For Yourself

Quite simply: The WordPress products that took off were solutions we built for ourselves to solve a specific problem. 

For example: 

  • BackupBuddy was built after we experienced a server crash in 2010. We needed a way to completely back up and restore our own WordPress website, so the idea for BackupBuddy was born. 
  • iThemes Security came on the heels of experiencing a server breach, when the need for a better WordPress security solution became obvious. 
  • iThemes Training courses like SEO Bootcamp and Google Analytics Bootcamp were launched because we needed this type of training internally. 

I can think of other examples outside of iThemes, like Restrict Content Pro. Over the course of that acquisition announcement, I learned that RCP was built out of Pippin Williamson’s need for a membership solution. 

3. Your Customers Likely See Your Product Differently Than You Do

One of the more interesting revelations was realizing customers often see the benefits of a product differently than we did. Often, there was a problem the product solved or another major benefit that we weren’t seeing, so we were missing an opportunity to highlight that benefit within our marketing efforts.

The best and only way to figure this out was to actually talk to customers. Interview them. Conduct meaningful surveys. Find out what you’re not seeing. Don’t guess.

Ultimately, knowing how your customers truly see your product better shapes and informs your marketing messaging, the copy in your sales pages, the emails you send, the ads you run. And it can help you focus your development efforts in a better direction. 

4. Simplicity and Clarity Always Win

Donald Miller says The brand that communicates the simplest is going to win.”

I bought into this idea, fully: Simplicity and clarity are the things that will set you apart from your competitors. And I have example after example to prove why he’s right.

In reality, though, it isn’t easy to be simple or clear. Maybe it’s even more difficult in the tech world, where building a product doesn’t automatically mean you know how to effectively market it.

I have learned that the pursuit of clarity and simplicity requires a few things:
  • Willingness to cut out anything unnecessary
  • No shortcuts
  • Intentionality
  • A lot of WORK

5. The WordPress Marketplace Evolves Quickly. Your Business Should, Too

We all know that WordPress is constantly changing. (Hello, Gutenberg!) This change (well, like all change) is always met in three ways: 

  • Resistance
  • Ambivalence (my personal favorite)
  • Acceptance 

The way WordPress core changes will impact WordPress businesses. There’s always the chance that the features you’ve built into plugins or themes may eventually become part of WordPress core. Or the functionality you’ve built as your product may become obsolete altogether. That’s a scary prospect, of course, bringing a level of uncertainty that isn’t for everyone.

We felt the challenge of WordPress change deeply at iThemes. After all, how do we work day-in, day-out improving our products and still be active in the wider WordPress community? How do you do both?

There’s no easy answer, but I can say for sure that staying involved in the wider WordPress community means keeping a better pulse on how WordPress is changing. 

This means:

  • Going to WordCamps
  • Actually getting to know our customers
  • Being active in WordPress.org support forums
  • Contributing to WordPress core
  • Building an interactive community of our own at iThemes Training
  • Building friendships with other WordPress business owners

While the challenge of change will always exist in a rapidly-changing industry, we learned we had to do what we could to stay relevant and continue to innovate. That often meant change within our organization and the products we offer. It meant pivoting to products that reflect the movement of both the WordPress community and the WordPress business ecosystem. 

6. Customers are Real People, Not Just Revenue Numbers

I remember reading something once about the limits of our comprehension when it comes to large numbers representing actual people. This awareness is also a monumental task when it applies to scaling a business and marketing: Each account represents an actual person with hopes, dreams, disappointments, and frustrations.

It can be difficult to hold the enormity of this continually, and I’ll be the first to admit it’s easy to get lost in charts and projections and forecast goals, losing sight of the faces behind all those numbers. 

At the iThemes office, we had an entire wall devoted to the pictures of customers. Every time I walked down the hall, I seemed to land on a new face. For a while, in the office break room, we had a TV that displayed the gravatar of the latest purchase (you never knew WHAT you were going to see). But these small efforts seemed to help remind us of the people behind the profits. 

7. Embrace Competition and Collaboration 

Not long after I started at iThemes, Cory Miller, our former CEO, hosted a “Friends of iThemes” event that included the owners of several other competing businesses. At the time, since I was new to the culture of WordPress, I found it a bit odd that competitors would meet up to talk through their shared challenges and successes … and just hang out. This was my first introduction to a rebuttal of the idea that just because you have competing products you can’t collaborate. 

One thing I’ve learned about the WordPress community is its generosity. I think this speaks to the fact that WordPress business owners, in general, truly want to help their customers. And of course, have a profitable business. We might as well work together.

8. Consistency is Key

All too often, we abandon endeavors if they’re not an instant success or if we don’t see instant results. But I’ve learned that some things take time. (In fact, I have a poster of this quote in my office to constantly remind me.)

Because business can happen at such a breakneck speed, and goals (especially revenue goals) can come with a ton of pressure and urgency, it’s easy to give up on marketing endeavors that don’t instantly succeed. 

That’s why it’s important to make informed decisions on what marketing initiatives are the most important, and commit to them. Really commit to them, and show your commitment with consistency

If I learned anything at iThemes, it’s that content, SEO and email are the secret sauce to great online marketing, especially for WordPress products. But these things take time. They take time to plan, time to produce, time to see results. And more than anything, they require consistency. 

  • Send an email every week, no matter what. 
  • Publish a blog post every weekday, no matter what. 
  • Keep optimizing your old and new content for SEO. 

Don’t give up. It takes time to see the payoff. 

As Gretchen Ruben says, “What you do every day matters more than what you do every once in a while.”

9. See Failure & Mistakes as Opportunities to Learn & Grow

A “growth mindset” culture requires one key philosophy: Failure and mistakes are an opportunity to learn and grow. 

Simply:

  • You can’t innovate without failing
  • You can’t learn without making mistakes

I’ll admit it outright: I’m a perfectionist. To the MAX. But it’s been one of the greatest challenges of my personal (and professional) life–putting down the heavy shield of perfectionism. 

It’s no secret that we made a few mistakes and had a few failures at iThemes. Some of these mistakes impacted our customers directly, other times we felt the failure internally. 

But each and every one of those things laid the foundation for us to ask the incredibly important question of “why.” Having those incredibly difficult conversations helped us take the mistakes and failure to learn, grow and do better. 

When it comes to mistakes and failure, own up. Communicate the hard truth, even if it means sending an email to your customers. Don’t sweep these things under the rug. Even if it’s painful at first, your team (and your customers) will ultimately respect you all the more for it. There is no pathway to trust without transparency and honesty. 

10. Personal Development Matters as Much as Business Development 

Ultimately, if I learned anything at iThemes, it was myself. When I started at iThemes back in 2011, I had no idea how much I didn’t actually know myself … or what I wanted. 

Most jobs aren’t exactly the avenue for introspective endeavors, but I was handed several resources that helped me learn about my strengths. 

For one, each team member got a StrengthsFinder assessment. 

I learned my StrengthsFinder strengths (or themes) …. 

Another strengths assessment is the VIA Character Strengths. Here are mine for that one:

Ultimately, knowing your strengths helps you sharpen them. When you know where you excel, you can work in your sweet spots. Knowing your strengths also helps you know when you’re working outside of them. With the knowledge of strengths, you can build a better team, where individual team members have complementary strengths. It also helps you see different perspectives, motivations, and priorities. 

All of these lessons helped me realize that personal development matters as much as business development. Work on yourself. Know yourself.

As Thoreau said, “Know your own bone. Gnaw at it, bury it, unearth it, gnaw it still.” Being a self-aware person helps you correctly frame all your motives, reactions, and decisions. This can’t be compartmentalized from professional life.

Wrapping Up a Decade + The Journey Ahead

More than the work and what we accomplished, I’m grateful for the friendships. We climbed trees, we rafted rivers (and fell out), we explored new cities, and we built some kick-ass WordPress products together. I’m thankful to be working with you every day, awed by your talent, your hard work, and your gif game. 

[Press play and continue reading]

To the iThemes team:

  • I’m grateful to Matt Danner, our General Manager, for seeing the potential in me, for teaching me how to shoot a bow and arrow, and for being a kindred spirit about things like finding personal solitude in the woods and drinking good chai. Also, congrats on the Emmy!
  • To Patti, Painkiller, made of pure gold: YOU are the glue. Your thoughtfulness is unmatched. Your kindness and generosity never left even the smallest detail untouched. I miss our walkabouts and conversations dearly. If I ever find myself barefoot on a beach in Hawaii again, you’ll be my first thought. Never stop exploring!
  • To Chris Jean, Wearer of Many Hats: Pizza Parties Forever! You are the most intelligent human I know. Keep thinking, keep baking, keep the cats happy.
  • Saylor Rain: You make all of us (especially Celine!) so proud. I can’t wait to see all the places you’ll go! (With a mink coat). Where do I buy a pass to the flower farm?!
  • Elise: In the nine years I’ve known you, I’ve always seen one consistent thread: you are made for great things. Thanks for all the cakes and commas
  • Sarah: I stand in awe of your spreadsheet skills. Thank you for always being so consistent and patient. And for doing it all while raising 3 boys!
  • Michael: Learner, Grower, Activator, Woo. You inspire me so much to never stop learning and asking questions. Plus, you like cool tunz!
  • Lewser: I would never have known so much about goats without you. I’ve enjoyed getting to work alongside your greatness. Live free and DIY.
  • AJ: Your caffeine intake is a thing of wonder, along with your webcam resolution. Wishing you all the best!
  • Timothy: What a cool thing it has been to get to see your talent expand. Winner forever of Zoom backgrounds. A Paul Hollywood handshake to you, sir.
  • Rebecca: Oh, Canada! Knit on. And take down the patriarchy.
  • Yobani: So glad we got to work together! Thanks for always being so helpful and for the taco recommendations.
  • Thomas: Thanks for your tireless work in supporting customers. I truly wish you all the good things … and a new Rubix cube.
  • Ronald: Afscheid! Still hoping to one day visit the Netherlands. Thanks for being such a great coworker and for all you’ve done for iThemes. Oh, and for the Stroopwafels.
  • Nathan: You taught me so much about WordPress! Thank you for being such a generous teacher and advocate for iThemes.
  • Curtains: I’m bummed we didn’t get to work together longer, but I’m excited to see where your experience and inquisitive nature takes you!
  • Schmatt: Thank you for always having such a bright, helpful, positive attitude. Plus, you brought us the world’s best no-bake cookies. (Thanks, Kels!)
  • Josh: I was always so impressed by your work ethic and positive attitude. Thanks for bringing your skills to iThemes.
  • Jenny: I’ll never forget your story about 9/11. That one will stay with me forever! Thank you for sharing.
  • Jared: While we didn’t get to work together that much, it was cool to see your hard work on RCP. Now, if I could just get a button to cancel my account at a certain online meal planning service …
  • Daphne: I was so incredibly impressed at how you finished a web development program while being a mom while working a full-time job. You are an inspiration.
  • To all the awesome folks at Liquid Web, including Joe Oesterling, Carrie Wheeler, Terry Trout, Mayra Pena & Misty Combs: Thank you for preserving iThemes and giving us a new home to thrive. It was a pleasure getting to know all of you!
  • Lindsey Miller: I must include you among this list of gratitudes. We’ve had so many amazing conversations I’ll cherish forever. I’m so thankful for your friendship and encouragement all these years.
  • Finally, thanks to Cory Miller, our former CEO, for giving me a place to learn, grow, and kick trash cans. I owe so much to you. 

Lastly, I’d like to give a shout-out to all the people out there who may be more comfortable behind the scenes of a business, content to do the work. Don’t try to fit into a mold. Build your personal brand, or refuse to do it out of principle. Seek out other interests besides business. Read for pleasure, take walks, have a hobby. If you despise social media or find it a waste of time, don’t do it. 

At the end of the day, at the end of a decade, only three things really matter:

  • Progress 
  • Passion
  • People

Pulling For Our Wishes

I’ll never forget the sunset Tuesday night. Driving home, the space just above the horizon line was glowing pink and orange. A line of heavy clouds obscured the upper portion of the sky, leaving just enough space for the light to get through. The sun slipped down, revealing itself for a few moments, a huge orb of light.

My view of the sky wasn’t perfect or full. Buildings and gas stations and warehouses blocked the sight, and I sped up, weaving in and out of traffic, hoping the highway onramp would unfold a better vista. But, by the time the stoplights cycled, the colors were already fading. I looked over, aware of my hands on the steering wheel, trying my best to match words to what I was seeing, the way blue and purple washed into pink and yellow, a watercolor western sky.

It was one of those sunsets that seemed distinct from all the countless others I’ve witnessed. I felt lucky to have seen it — a true, unexpected gift — it only lasted for a few, fleeting moments. Had I not left work ten minutes early, I would have missed it completely.

For the rest of my commute home, I turned the radio off, getting lost in anticipation. It was election night in America.

I realize now I’d just assumed I’d be standing in front of a TV when the results were finally called, moved once more by the ideals of hope, democracy, unity, equality, and a brighter future. The voters would speak, rejecting fear and hate. I was ready to have my faith in the country restored.

***

The last few days have been hard. I didn’t anticipate how deeply this election would emotionally affect me: sadness, anger, grief; the realization of profound misunderstandings, deep divisions.

I hoped to find some solace by going to the park. The sun did come out today and yesterday, as it usually does, to remind us that nature does not bend to our moods. It was actually a beautiful day, warm sunlight, a blue sky. The colors of fall get brighter, more saturated — reds, oranges, yellows.

There’s a particular smell right now, when you’re walking through the woods — crisp, spicy, earthy. There’s a small window of time before the leaves on the ground get damp and begin to decompose. That’s another smell; it’s both sweet and savory, like the smell of red wine.

I made my way down the trail, beginning in my favorite part of the park. The branches of the younger oaks thread over the path; sunlight falls in a patchwork over the ground. A breeze picked up and the leaves rustled, and I stopped, watching: the sight of those yellow leaves falling all around, fluttering to their final resting place.

I walked mostly, running only for a few minutes. My leg muscles ached and my body was too tired. My mental energies have been exerted elsewhere, and there wasn’t enough left.

I passed several people — people with their dogs trotting ahead of them, a man in a business suit and sunglasses, another jogger. That we waved to each other, smiled, as strangers, lifted my spirits. Maybe we’d taken to the park for similar reasons, even if we had cast our votes differently.

Near the first mile marker on the trail, there’s a sculpture of two children pulling on a giant wishbone. The top of the wishbone arches over the path; each child pulls on their own end, on opposite sides. Their bodies are frozen in the struggle, their arms stretched up, squatting into their effort.

Near the first mile marker on the trail, there’s a sculpture of two children pulling on a giant wishbone. The top of the wishbone arches over the path; each child pulls on their own end, on opposite sides. Their bodies are frozen in the struggle, their arms stretched up, squatting into their effort.

The race looks equal, and you can’t tell which one will win, where the bone will crack above them. If I have one criticism of the work of art, it’s that the children look too similar; they’re identical in fact. Neither looks to have an advantage.

I’m not sure the world is actually like that, that there’s a fundamental fairness promised to everyone. Not everyone is an advocate for equality, especially when the disadvantages of one actually benefit another.

Can the wishbone ever break evenly, divided down the center? Can there be more than one winner? Can we all get what we want? The artist didn’t reveal what happens, deciding instead to immortalize the moment just before the outcome of the competition.

And so we toil on, pulling for our wishes. Maybe the wishbone hasn’t cracked quite yet.

Tell the Trail, My New Memoir, Is Here

About three weeks ago, I sat on a rock by a river in Colorado, typing up a status update to publish on Facebook. It was a sentimental date for me—two years ago to the day, my new book, Tell the Trail begins.

After the post went live, I got up, brushed off, and took a look upstream. The river ran in a swift current around me, even though the water level was much lower than during the summer rafting season when the snow melts off the peaks.

Up the hill, after a steep climb up the banks of the river, I found a monument. It was a huge boulder that looked more like an abstract sculpture, the center hollowed out to form a hole.

On the top of the rock, a plaque was cemented into the surface of the stone.

“Life can only be understood backwards, but it must be lived forwards.
–Søren Kierkegaard”

When I read the words on the plaque, I was overcome with emotion. “Life can only be understood backwards, but it must be lived forwards.” A quote from the philospher Kierkegaard.

Under the quote, names and dates were listed to honor rafters that had died on the dangerous stretch of river.

I stepped back, realizing it: I’d traveled over six hundred miles to finally find my answer.

What’s the Book About?

“What’s the book about?” That’s one of those questions that has followed me around the past few years, along with “Why publish your journals?” 

I’ve tried out a few different answers to the What’s it about? question.

“It’s a memoir.”
“It’s just my journals.”
“It’s about learning to be mindful and live in the present.”
“It’s about life.”

The truth is—I can’t reduce Tell the Trail down to just one sentence. I’m still in the midst of my story, living each day, feeling my way through my own narrative.

I’ve wanted to capture every single detail of my life, everything from the mundane to the extraordinary.

Looking back on the last two years, a lot has happened. I published my first book. I turned thirty. My best friend, Emily, got pregnant and had a baby. I traveled from the East Coast to the West Coast, put my feet in both oceans. I learned a lot, I struggled a lot, I celebrated a lot. I’ve wanted to capture every single detail of my life, everything from the mundane to the extraordinary.

I know now that one of the callings of being a memoirist is committing to the work of gaining clarity about your life’s story. Life must be lived forwards; we must live diligently and earnestly, paying attention. In having a record, I can look back, understanding.

Why Publish Your Journals?

We aren’t usually interested in anyone’s journals or diaries until they’re famous. I’ve combed through the journals of Thoreau, Sylvia Plath, Virginia Woolf, and Joyce Carol Oates—some of my favorite writers, interested to see how their private lives flowed into their art. Maybe there will always be something a little thrilling about gaining any type of insight into someone’s innermost thoughts and struggles. We see ourselves mirrored back in the words of others; for once, we can relate.

Journaling has been my mirror and compass, reminding me that writing is my passion. By keeping a journal, I’m learning the sound of my own voice. 

There’s a reason journal-keeping is used as a tool for introspection and contemplation. Journals are much more than a personal history book. My journal has been a safe place to sort out thoughts and feelings and a way for me to identify meaning.

My journal reflects myself back to myself, reminding me what’s important. Reading back through my journals, I have a clear picture of significant events. I’ve learned worries and feelings come and go. By keeping a journal, I’m learning the sound of my own voice.

My journal has been a compass, pointing me in the direction of pursuing my passion: writing. Writing gives me a way to convey an inner life I don’t always know how to express otherwise.

So here it is. Tell the Trail, my new memoir.

So here it is. Tell the Trail, my new memoir. Here are my journals, imperfect just as I am, bound up between two covers. Here’s my own personal history book, shared in dedication to living, to the act of remembering.


Having kept a journal these past two years, I’ve found each day is special and significant, brimming with meaning. My journals have been a safe place to unwind the threads of my experiences and weave them into a larger story, a bigger picture of my life. Now, combing through the archives of a full year, to have detailed, daily records of what I saw and felt and thought, to trace out the horizon line of my own internal landscapes, I’m overcome by the width and depth and breadth of life.

I’ve learned I must be a diligent scribe—and student—of my life. And maybe—I need to let other people read what I’ve written, what I’ve found.

Maybe the record of one life will knit itself into the fabric of someone else’s.

Available now on Amazon.com

Get a preview here.

Buy Tell the Trail

Improvised Trails

I ventured off the paved path today, into the thick brush of the park. Off to the right of the walkway, a slight parting of the trees revealed a narrow dirt trail. Where did it go?

A few footprints were pressed into the damp mud ahead of me, so I wasn’t the first to follow my curiosity. I wondered who else had been here before me; maybe the trail was already familiar to them, or maybe they had set off exploring the unknown, like me.

I made my way forward, ducking under limbs, pushing branches out of the way, navigating around vines with thorns. A few paces in, I stopped, surveying the scene—a thick, wild wood had engulfed me: the scent of evergreens, fresh and new; trees with the first hints of green leaves; tall brown grass.

Looking around, I was reminded of being a kid, exploring the woods in front of our house. Maybe it was because there was something mysterious and enchanted about the interior of the park, like a secret garden, long overgrown and forgotten.

Looking around, I was reminded of being a kid, exploring the woods in front of our house. Maybe it was because there something mysterious and enchanted about the interior of the park, like a secret garden, long overgrown and forgotten.

I continued on my way, stepping, climbing, exhilarated. I wasn’t sure where I was going, exactly, and maybe that was the thrill.

Up ahead, the trail forked and I considered my options. On one side, a tree had fallen over the path, most likely during the ice storm last fall. On the other, the trail seemed to fade into thick brush.

I chose the fallen tree, mainly because I wanted to climb over it. And just as I crested the trunk, a knobby branch caught my pants and ripped a hole in them.

I leaned down to inspect the damage—it was a jagged tear, about 3 inches wide, on my upper thigh. The fabric was tattered and irreparable.

I laughed to myself, thinking this is what I get. I get a hole in my favorite pants because I needed an “adventure.”

I heard voices up ahead and I could make out the outline of two women walking on the other side of a line of trees. I could see the black pavement of the walkway—I’d made it from one side of the park to the other, I just needed to navigate the last bit of brush.

When I finally emerged out of the woods, it was to an open clearing in the more habitable part of the park, right in front of one of the more popular playgrounds. I tried to act casual, like it was a very normal thing to have done—duck out from behind a few branches, off an improvised trail, looking only slightly disheveled, with torn clothes.

I rejoined the pavement, walking on. From behind my sunglasses, I glanced over at the people sitting where they were supposed to sit, at picnic tables or under the pavilions, or swinging their children on swings, enjoying a sunny afternoon in the park.

***

 

 

Monhegan, Out-To-Sea Island

Low tide. The ocean recedes, revealing a landscape that is usually hidden underwater—sea moss-covered rocks, their texture like velvet, brown and bright green and yellow. Later this evening, when the tide rolls back in, the water will overtake them, leaving just the ancient gray granite above the surf, stacked high, unmoved, unchanged, for centuries.

This morning, the lobster boats idle in the distance, swinging out into arcs, than stopping. Whether they’re collecting their traps or setting new ones, I can’t tell. Brightly colored buoys are scattered everywhere in this cove, like sprinkles.

This morning, the lobster boats idle in the distance, swinging out into arcs, than stopping. Whether they’re collecting their traps or setting new ones, I can’t tell. Brightly colored buoys are scattered everywhere in this cove, like sprinkles. Every color and combination you can imagine—green with white, yellow and red, blue, neon green. Some are so close to the shoreline now, in low tide, I wonder if I could walk out onto the rocks to inspect how far the ropes extend down deep into the surprisingly clear water.

“Maine has the highest number of elderly people per capita,” the retired judge from Houston told us yesterday. After they offered, we joined them at their picnic table in the shade. We were surprised to hear they were from Austin, and we talked more commonalities—sports, the first Longhorns game of the season this weekend, hating Interstate 35.

We sipped on our sampler flight of four beers outside the Monhegan Brewery, deciding which one was our favorite. I preferred the pale-colored Kölsch and Jacob’s was the black IPA. I’d also ordered a small glass of their house ginger beer, which was my favorite out of them all. The taste of it was spicy and cool and refreshing, perfect after the rocking hour-long boat ride and the long hike we’d taken along the island’s east coast.

We woke up early that morning to catch the 9 a.m. ferry. The ferry runs twice a day out of New Harbor, once in the morning and again in the afternoon, making it a perfect day trip—five hours to explore the island, which is just enough to walk from one end to the other. When we left, a heavy blanket of fog covered the harbor and I assured myself surely it would burn off when the sun got hot in the afternoon.

We got to the ferry early enough to choose a seat on the top deck with a view. A handful of other people were already there, like a couple that sat in the very back with their wire fox terrier. All of the wooden-bench seats eventually filled up—elderly couples with broad-rimmed hats and compression stockings, a group of four rowdy tourists about our parents’ age, and two couples that looked to be our age, or younger.

I snapped a few pictures over the guard rail, looking out into the harbor. The fog erased the horizon line, so the scene was otherworldly—bright white and yellow light, the water a mirror; a few lobster boats anchored into the water.

new-harbor-fog

The fog erased the horizon line, so the scene was otherworldly—bright white and yellow light, the water a mirror; a few lobster boats anchored into the water.

The hour-long trip to Monhegan was shrouded in fog; it never let up. Visibility was limited to a few feet beyond the boat’s sides, so you could make out the rippled surface of the water, and our wake. I kept my eyes closed to avoid getting sick, just letting myself feel the motion of the boat moving across the water, back and forth, sometimes forward and backward. When I did open my eyes, it really was a beautiful, mysterious scene: the bright light diffusing through a fine mist of tiny water particles, dispersed through the air.

The couple in the seat ahead of us soothed their crying baby and someone behind us wondered out loud “shouldn’t the gentle rocking help?”

***

We landed on Monhegan Island in a little over an hour’s time. I was sad to miss the view of the island as we arrived, since the fog obscured everything. Once we got off the boat, visibility increased, and you could make out the inns and shops and houses—and the immediate feeling of history: upright wooden-shingled colonial houses, brightly-colored front doors, stained brick chimneys.

monhegan-cottage

I brought one of my Maine guide books and circled the places on the Monhegan Island map it mentioned: follow the Burnt Head trail, then turn north on the Cliff Trail to Squeaker Cove, then head back west through the Cathedral Woods, back to the village. A short walk (and a few wrong turns) lead us to the first sign, so we set off.

What we found was awe-striking: a hike through a dense forest that eventually led up and over rocks to five separate panoramic views of the cliffs and the ocean. “It’s like something out of a movie,” Jacob said. “I just can’t believe we’re on an island.” We took a few minutes to sit down on the rocks overlooking one of the cliffs. A man in a brightly-colored orange shirt sat on the rocks in the distance, the only foreign color in the scene.

The sound of the surf roared down below, crashing on the rocks. I remembered something the guide book had mentioned: this is were you keep a healthy respect for the ocean.

The fog hadn’t completely cleared, so you didn’t get a complete view of the ocean’s horizon line, but it was enough to see the jagged outline of the cliffs and the pine trees clustered at the top. The sound of the surf roared down below, crashing on the rocks. I remembered something the guide book had mentioned: this is were you keep a healthy respect for the ocean.

We hiked on, doing our best to follow the illustrated map—climbing sometimes vertically over rocks, then down steep ledges to continue on the trail. We passed a few other hikers—groups of elderly people with hats and belted shorts and walking sticks. “If they can make it, we can,” Jacob joked. I laughed, out of breath.

monhegan-hike

The last part of the trail heads through the Cathedral Woods, a thick, shady forest that runs through the interior of the island. I wondered how a complicated landscape ended up on an island, which seems like an abbreviated version of the mainland—but Monhegan boasted all the complexities of a rich geography, and the forest seemed to mark it’s own legitimacy, in case you had any doubts. It was cool in the forest, and I could understand its namesake—the cathedral of tall trees overhead; a sacred place all in its own.

cathedral-woods-monhegan

After two hours of hiking, we were hungry. I’d packed the same picnic lunch as I have every day this week—sandwiches, crackers, hummus, cookies, the added treat of a brown-spotted banana. We hiked up the hill to the lighthouse and found a bench overlooking the island. From the spot, you could see Manana Island off in the distance, a cemetery with white headstones, the cluster of rooftops in the village center.

I stopped to snap a few pictures of the man painting a small canvas on his portable easel. He stood with his back to the path, working paint with a tiny detail brush. I imagined what it would be like up here, painting, an audience of passing tourists that stop and watch you work, appreciating your efforts to capture the scene.

***

We left Monhegan content, tired, a little sunburned, and full of beer. Jacob ate an ice cream cone on the walk down to the ferry and I took a few licks; it was melting quickly in the afternoon sunlight. The fog did eventually burn off, enough for us to get the view of the island as we left and headed back out to sea.

On the ride back, we spotted seals and porpoises and everyone cheered and clapped as sightings were announced. I didn’t close my eyes this time: I wanted to remember it all, take it all in, this day spent on the island out-to-sea.

monhegan-island-ferry

 

Our Own Trails

I set off on the trails, alone. I wanted to make each loop, take them all in, mark my progress on the map. It took a little under an hour, just enough to be full and satisfied with my portion.

I went early enough to escape the summer heat, to pause overlooking the creek in a fleeting cool breeze. How lovely it is to be under the shade of tree branches, with nothing but the sound of gravel underfoot, moving forward.

My secret landmarks still stand, quietly—the giant tree with the enormous, ancient trunk; the long bench with the mysterious L.M.B quote; the lonely gazebo out in the tall grass; the angled red rocks near the creek’s shoreline. Maybe one day I’ll match them up in my mind with their corresponding trail letter and color, make them serve as a true indicator of my location.

I took time to explore, to get off the path. I wandered down near the pond in damp mud, then climbed down on both sides of the creek to walk the red-rocked banks. On one end, you can see the metal bridge in the distance, on the other, the stream winds away from the boundaries of its stony beach.

Instead I found the place full and brimming with summer—all green leaves and wildflowers in golden sunlight. It’s the most beautiful place in this city and I’m content to think it’s still a wild, hidden treasure.

On the climb up from the creek, tufts of dogwood cotton had collected along the outer edges of the trail, as if they’d been swept from side to side to clear the path. They’re the last remnants of spring, a season I missed entirely at Martin Nature Park. Instead I found the place full and brimming with summer—all green leaves and wildflowers in golden sunlight. It’s the most beautiful place in this city and I’m content to think it’s still a wild, hidden treasure. It’s vast enough to feel like you could get lost, but small enough to know all the well-marked trails will lead you back home.

I passed a few people along the trail, all with a nod and “Good morning.” Most were alone, like me, and I wondered as we exchanged glances—do you need this place like I do? Do you need the tall trees with branches curved into a canopy of shade above, the open meadows that rustle with tall grass, the creek that ripples and murmurs over eroded stone?

Yes, I think. I know we both do.

And we continue off in our own separate directions, down our own trails.

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