My Pathless Path: From Traditional to Independent Journey

The first 6 months after 6 years at Miro.

Mar 03, 2024

I’ve recently finished reading the book “The Pathless Path” by

. As an additional self-reflection, I decided to use the momentum of almost 6 months since I left Miro to summarise the insights from this book, connect them with thoughts that resonated the most, and share them with everyone who might be experiencing something similar in their lives and career journeys.

I divided this story into several parts.

Part 1: Preparing to Step Into Uncertainty
Part 2: Transition from Traditional to Independent Journey
Part 3: Almost 6 Months on a “Pathless Path”
Part 4: Looking Into The Future
Bonus 🎁: 10 Learnings That Helped Me Along The Way

Each part will be filled with quotes and insights from “The Pathless Path” book that I wish more people could benefit from. Let’s start 👇

Floods (L'inondation).1893, Charles Guilloux

Part 1: Preparing To Step Into Uncertainty

My career journey was always well-strategized, predictable, and some people who know me would say “Kate, you were always doing everything right”. But what is right? Is it a certain confirmation of the collective mindset and norms? For me, it was exactly that — following the path of accepted role models.

It started from school: being an “A-grade” student, doing everything “right”. Then university: choosing rationally the most business-oriented specialty, moving a bit away from my creative nature. Then choosing a profession: connecting creative + business parts led me to UX design. Finally, getting a dream job in an emerging unicorn — becoming one of the first Product Designers at Miro.

My growth journey at Miro was also well-strategized and linear, however, some people said it looked exponentially fast. In total, I had 4 titles over 6 years in one company, in that order:

Product Designer (Growth, Enterprise, Design System) → Lead Product Designer (Growth and User Research) → Product Design Manager (Growth) → Head of Growth Product Design.

Looking back, I see that all these strategized career decisions made me deeply dependent on the feeling of “certainty”. However, the transition to a leadership role helped me realize this is a problem: the number of things that I couldn’t control increased exponentially, while my ability to manage them was still developing. That was a pivotal moment that helped me start diving deeper into myself through psychology.

Deep work has been happening for the last 3 years with personal emotions, limiting beliefs, and other parts that started opening up new sides of myself. It led me to start thinking about one difficult and uncertain question — what’s next?

At this point, I’d like to refer to the foundation of Paul’s concept and define the “pathless path”. I didn’t know that term when I was considering a shift, but I wish I knew it earlier than later:

“The pathless path is an alternative to the default path. It is an embrace of uncertainty and discomfort. It’s a call to adventure in a world that tells us to conform. For me, it’s also a gentle reminder to laugh when things feel out of control and trusting that an uncertain future is not a problem to be solved.”
Paul Millerd, “The Pathless Path”.

Landing it on my personal experience, all the steps that led me to that point were associated more with a default path or “doing things right”. But as Marshall Goldsmith says: “What got you here won’t get you there”.

This is why the thoughts about leaving my full-time job felt initially “wrong”. However, I started feeling that I was reaching the limitations of that default journey, and I needed more space to figure things out.

One of the most important challenges that I consciously wanted to face was how to deal with higher levels of uncertainty with a sense of peace and inner stability. Now it seems to be a necessary foundation for any other experiments throughout the lifetime.

“Instead of thinking about what you want to do with your life, you default to the options most admired by your peers. C.S. Lewis warns that, “unless you take measures to prevent it, this desire is going to be one of the chief motives of your life, from the first day on which you enter your profession until the day when you are too old to care.” He believed “any other kind of life, if you lead it, will be the result of conscious and continuous effort.”
Paul Millerd, “The Pathless Path”.

Learnings on the Preparation Phase 🙏

Create space for recovery before taking a leap. This can be a longer vacation, sabbatical, or a 3-day silent retreat that was most influential for my inner state last year.
Lenny Rachitsky
shared that his 1-year sabbatical from Airbnb turned naturally into things he’s doing now.
Prepare yourself psychologically. Dealing with uncertainty and instability is incredibly hard. For me, it took 3 years of weekly sessions with a psychoanalyst to start building a stronger mental foundation for a dramatic shift.
Think of a financial pillow. In reality, this is the most difficult thing to predict in a situation of potentially unstable income. In my case, I have a mortgage in one of the most expensive cities in Europe, and mentally that was hard to process. However, it’s an opportunity to reconsider expenses and prioritize things that matter. Everyone has different conditions and resistance to financial instability, but a lot of people think that only lifelong savings can be a signal to move forward. If that pillow is too comfortable, then it can limit the person from developing a new business idea faster.

Part 2: Transition From Traditional to Independent Journey

I love how Paul describes his first steps into the new path as “launching experiments”. That was exactly the core intention and desire in my case — to experiment with several new career trajectories beyond a traditional path. I started with creating a “Personal Painted Picture”, the tool that I also use in my coaching practice to “zoom out” and build a foundation for the career path considerations.

My Personal Painted Picture helped me prioritize 5 paths that I can start exploring right away while searching for what I care about the most. I knew that the variability of activities and a generalist mindset were the things I’d like to translate into this experimental phase. Surprisingly I encountered a fresh post from

Leah Tharin

about her solopreneurship. I'm grateful to apply the wisdom of others who led by example while making the solo paths possible.

“On the pathless path, however, optionality can pay consistent dividends because you are not holding out for another job but leaving space for a little more life.”
Paul Millerd, “The Pathless Path”.

While someone from the outside could have suggested narrowing it down and saying no to some things that don’t give immediate results and income (like Growthmates), my inner voice told me to keep moving forward with all of them with commitment and consistency. Luckily, I had strong accountability partners across the majority of these activities —like

Viktoria Kharlamova

with whom we committed and finished a big industry research that turned into an amazing Onboard.report that over 2000 people found useful. Over time, I also realized that Growthmates guests turned into partners and connections that gave me a lot of energy, which is more valuable than immediate income reward.

“It was the end of a three‐month period where I had felt completely alive, spending my time learning, creating, solving problems. But along with greater freedom and self‐determination came the anxiety and insecurity of never really knowing if you were working hard enough or doing the right thing.”
Paul Millerd, “The Pathless Path”.

During a transitionary phase, high-energy states can be followed by anxiety, as your brain still remembers the past and tries to hold on to that. Being in the present feels insecure. Then flashbacks like “maybe I need to search for a stable full-time job” can appear as a lifebuoy, but in fact, this is a clear signal to move forward on the pathless path and learn how to deal with higher levels of uncertainty.

Learnings from the transition phase 🙏

Reflecting on the emotional response from every activity. After any advising session, AMA, podcast recording, or deep focus work, I’m trying to measure emotional state on a scale from “draining” to “fulfilling”. It helps to realize which activities give more or less energy.
Having accountability partners. In my case, I was lucky to find them everywhere. Starting from my partner and closest friends who are also interested in independent careers to the community of supportive partners whom I’ve seen only online. Both close and broader networks provide extra reliability and support. Thank you 🖤
Consistency and commitment. Space and freedom can create chaos. The discipline helps to turn it into a structured system of enjoyable daily work routines. Like with this newsletter, I publish new things on Sundays at 5:30 pm CET. Today is that day, and I try to stay consistent and committed to that routine.

Part 3: Almost 6 Months On a Pathless Path”

Today is the beginning of March 2024. The sixth month of my pathless path has begun. While I still feel a lack of stability, I turned 4 out of 5 activities into income sources. I don’t have income predictability yet, but I have a more precious thing — freedom.

“When I build websites, launch a podcast, create online courses, use marketing tools, and hang out with friends on Twitter, I am a kid again, sitting in front of that first computer.”
Paul Millerd, “The Pathless Path”.

That freedom opened up a lot of creativity, and I started investing in working with Advising clients, creating Growthmates (the picture above from the last recording with

David Hoang

), running industry research projects, launching the first course, creating this newsletter, supporting others with 1:1 coaching, and most importantly — not forgetting to live my life.

I spend around 8 hours a day working or thinking about my new type of work, but it feels incredibly rewarding. Each type of work gives the creative aspect, and “the act of creation is the reward itself.”

Apart from that, I have time (and most importantly — energy) to have an intense, active, and healthy lifestyle. Every week I go to art exhibitions, visit cinema discussion club bi-weekly, practice yoga and pilates 3-4 times a week, cook almost everything I eat by myself, and spend a lot of time socializing with my husband and friends.

In a couple of weeks, I’ll go to Japan for 3 weeks, the longest trip I’ve ever had in the last 7 years. It’s a big investment for me, and I’ve been preparing for this trip for a couple of months. Vacation doesn’t feel like an “escape” anymore — it’s a conscious time investment and culture exploration.

“We started to recapture a youthful energy, one that enabled us all to take bold steps towards different kinds of lives. This shifts attention from focusing on saving for the future to understanding how you want to live in the present.”
Paul Millerd, “The Pathless Path”.

Learnings from the Current Phase 🙏

Experiment, reflect, and iterate smart. From the Product Growth practice, only around 50% of experiments are successful — the same applies to the professional journey. Not all opportunities have an immediate impact, and that’s fine. The common mistake is completely pivoting direction right after that. My approach — learn, reflect, and iterate smart. Combining it with the “consistency and commitment” rule helps me just keep doing things I find valuable, and soon they will present more return on investment.
Weekly self-reflection exercise. I dedicate at least 1-2 hours each week to strategic thinking that helps me constantly reflect and re-prioritize many things I’m doing. Being constantly in a “doing” mode is not an option for me anymore, as this “thinking” mode gives impactful decisions to inform what activities to invest in.
Treating art as a source of inspiration. This source is something I lost long ago, but now it’s time to give it back to me. I go to museums or galleries at least once a week to get inspiration from visual art — and it became a priority.

Part 4: Looking Into The Future

Once in December, I was on a plane, in the middle of a chapter of a book where I encountered the definition of success that deeply resonated:

“A person is successful if they have followed their own interests and talents to become the best they can be at what they care about most.”
Paul Millerd, “The Pathless Path”.

More specifically, the part about “what they care about most” opened up a fundamental question that became an intention for this year. If we get back to the picture with 5 directions, the intention is to continue experimenting with these paths, reflect on the value I can bring through them, my emotional response, and hopefully find a unique combination that I can do indefinitely.

“More important is the realization that finding something worth doing indefinitely is more powerful and exciting than any type of security, comfort, stability, or respect a job might offer.”
Paul Millerd, “The Pathless Path”.

I see a lot of dreams and tangible opportunities to realize them, while I want to listen carefully to my values, stay loyal to them, and “not trade these things for a bigger paycheck”. Another aspect that started thinking more deeply is understanding what is “enough”.

“Enough is seeing a clear opportunity that will increase my earnings in the short‐term, but knowing that saying “no” will open me up to things that might be even more valuable in ways that are hard to understand…Enough is having meaningful conversations with people that inspire me, people that I love, or people that support me.”
Paul Millerd, “The Pathless Path”.

Looking into the future, I want to take these intentions with me: