About a year ago, I realized I was ready for a change. I tremendously enjoyed working with my co-founders Dave and Mike and our team at Holstee, but I wasn’t happy and excited anymore on a daily basis. 5+ years of startup grind, the ups and downs, I was starting to feel it. Nothing was wrong with my company, but I was ready to close this incredible chapter and move on.
And so, at the end of 2015 I left and immersed myself in the big quest of trying to figure out what my next adventure will be. In contrast to past transition moments, when I tried to find another engagement as quickly as possible, this time I’m trying to enjoy it and learn about what makes a “good” transition. Over the last couple of months some insights have emerged that have shaped me and helped me navigate these unstructured times.
1) Transitions will most likely be a constant for the rest of my life. I can become good at it.
Transitions are these magical moments in life where everything is open and anything is possible. Yet, I found navigating that openness and dealing with that uncertainty to be tough. What I have learned over the last few months are two simple, yet for me, powerful insights:
First: Transitions will keep happening. This definitely isn’t the last time I’m going through one. My personal rule of thumb is that I’m trying to find a next adventure that I can commit to for at least 5 years. But after that, I’ll most likely be in the same spot again and will face another transition. While in the past people had one long career, I imagine mine will be a patchwork of projects and adventures. So, given the fact that I’m 34 years old, I probably have another 8 to 10 transitions ahead of me.
Secondly: I can become better at transitioning. The longer I’m in transition, the more I realize that there are many structures, tools, questions, experiences and exercises that make transitioning easier. And as I become more aware of what helps with transitioning, I can learn it, I can adapt it and I can become good at it. Even though there doesn’t seem to be much structured or easily accessible knowledge around it, I believe there is a science and art behind transitioning. I’m planning to write more about this topic, but one of the highlights for me lies in identifying and introducing the right transition habits.
If both of my assumptions turn out to be true, that transitions will keep happening and that there is an art and skill behind transitioning that can be learned, then there must be a huge potential and importance in understanding this area of life better.
2) This is not just about finding my next gig. This is where I grow.
In the past I tried to get through any transition as swiftly as possible. The transition solely existed to find another adventure, in my case often another startup idea. But over the last few months I realized that my perspective had been too narrow.
As I’m transitioning, I realize what an incredibly precious time this is, not just to look for future opportunities, but to grow as a human being in the present. When else do I have the time and space to reflect on my strengths, weaknesses, dreams, potentials and things I want to change about myself? When do I have time to actually work on my character flaws and become a better human being? When do I have the “luxury” to dedicate time to build positive habits? In “normal” work situations, these things always have to fit on the fringes: after work, on weekends, at retreats, on vacations. But the magic about transitions is that now I have all the time in the world to focus on growing not just my career, but more importantly my own human being. This is important, because it puts me more at ease when I don’t make visible progress on finding my next thing. Even then, this time is worth it.
As a consequence of this insight, I started to plan my transition life differently: away from simply looking at new opportunities, and planning more time for personal growth, for example by giving highest priority to daily meditations, writing and reflection time.
3) I won’t find my next adventure through reflection, but through smart experimentation.
When it comes to finding my next project, the advice I hear most often is “just follow your passion” or “do what you love”. While that advice seems to come easily (and I have given it myself), not many people talk about the logical, but much harder, follow up question: how do I find out what my true passion is?!
My original plan was to spend most of my transition in deep reflection: meditating, reading and writing. And then, over time, I would gain clarity what I wanted to do next. But Rownak Bose, a dear friend and mentor of mine, made me realize that whatever I will do next, I couldn’t know if I will like it (or even more so, love it) by simply thinking about it. While reflection can bring out my desires and interests, they are nothing but unproven theories. As I don’t know what I don’t know, it’s hard to predict how those theories will hold up in reality. So the only way to find out is to try.
I’ve realized that in order to “find my passion”, I first need to learn to create meaningful transition experiments. How can I test my gut feelings and instincts? How can I test in a thoughtful way, with the limited resources I have at hand? Can I do several experiments or just one at a time? I have mostly questions and no real answers at this point, but my sense is that there is a lot to be learned from the rapid prototyping and MVP approach in the startup world.
In my transition experiments so far, I have learned that I easily get excited about an end goal (e.g. I want to build a high-impact social venture). But then, am I equally excited about the path that leads there? Will I enjoy putting in the work to build that social venture? Because if not, it’s probably not the right goal. I see that happening to me easily and often. That the end goal looks appealing. But at closer look, the actual path to get there isn’t really for me.
4) I have to be ok with my past to choose a strong future.
While the transition is so inherently forward looking, I realized that in order to choose a future with confidence, I first needed to be ok with my past.
When I first started my transition, I realized that I had some grudges about the past I was carrying with me. Inside of me, I felt disappointed that I had left Holstee, not (as I had originally imagined it) after an acquisition or some big event, but in the middle of things. I was comparing myself to others, especially to entrepreneurs who were of similar age and had seemingly achieved much more success, especially financial success. Parts of me was still bitter about what happened with Sandbox. I wondered why some of my romantic relationships hadn’t worked out. While some of my friends were getting married, I was single at 33. And quite often I asked myself how in the world I had worked so much over the last 15 years and ended up with no savings at all.
But over time I realized that I had to face these demons, look at them very closely, and then let go of them, so that I could move on. About a year ago, Dave, Mike and I were fortunate enough to spend a morning with Seth Godin, who was incredibly generous in helping us figure out where to go next with Holstee. We had some regrets and questions about the past and were lingering on them: advice we ignored, wrong decisions we made, poor investments of our time and energy — the typical startup stuff. Seth’s advice was very simple, but struck us deeply: “just forgive yourself and move on”.
And so I tried to apply that same advice for my own transition and find closure with my past. I did this in the following ways:
I debriefed the last 10 years of my life. What has happened? What have I learned? What were highlights, what were lowlights? What should I continue doing? Here is the detailed debrief framework I used.
I debriefed my last venture, Holstee, together with Dave and Mike. Here is the venture debrief framework we used.
I wrote down a list of regrets, doubts and fears, both about the past and the present. I wanted to know the dark stuff inside of me and bring it out.
I cleaned up my apartment and got rid of a lot of stuff. It felt amazing and like a heavy burden falling off my chest.
I started to focus heavily on gratitude and appreciation. On the one hand, I tried to look at the debriefs above through a lens of gratitude, but I’ve also built daily habits of gratitude: after my meditation every day, I think about things I’m grateful for. And after my daily writing exercise, I usually close with 3 things I’m grateful for and 3 things I appreciate in myself.
I thought a lot about the question of what it means to “be enough”.
5) Transitions are about shifting from the urgent to the important. That’s why the right setup matters.
As part of my transition I have been thinking a lot about the urgent vs important matrix. I realized that my “normal” life, outside of transition, has quite different needs than my transition life. In my normal modus operandi I have a clear objective I run towards and I want to get shit done. My day includes meetings, emails, events, travel, projects, deadlines. It’s pretty fast paced and opportunities pop up along the way that I want to react to. However, transition life is different. I do not know where I’m going. And I need big chunks of time for these fuzzy things such as self reflection, learning, reading, and experimenting.
The big difference is that the stuff that matters in transition is by definition super important, but almost never urgent. Sounds dangerous to a professional procrastinator like me.
When first debriefing my transition, two months in, I realized that I spent most of my time with stuff, meetings, emails, projects, work, but hardly worked on my big transition goals. In short, I had gone back into urgent problem solving mode. In order to make any progress with my transition, I had to shift my setup consciously to go into a different kind of work mode. Here is how I created a good setup for focusing on what matters in my transition:
I try to reflect my priorities in how I structure the day: the first half of the day is focused on transition related activities, my habits and pro-active things I want to work on, while the afternoon is mostly free flow and reactive stuff.
I left NYC. By simply removing myself from where I usually live, many meetings, events, urgent local stuff naturally fall away or become irrelevant. It also provides me with an easy and honest excuse to decline things.
I made a list of things I usually say yes to, but during my transition want to say no to. For example I usually spend a lot of time meeting people, friends, introductions, just generally inspiring people. I reflected on the value of socializing and have come to the conclusion that what I need most right now are not deeper relationships, but clarity on my next step and personal growth. So I’m consciously saying no to meetings. Other things on the temporary no list include: conferences, events, most work projects, active participation in communities.
I have developed strict habits that support my transition, including meditation, writing morning pages, working out every day, debriefing every month, etc.
6) True expansion comes from nothingness
A few weeks ago I sat down and reflected on my first few months of being in transition. What struck me was that some of the most insightful moments were instances of total boredom and nothingness, like when I ended up on a 16 hour flight with nothing to read, no functioning tv screen and an empty phone and laptop battery.
It was in those moments when my mind expanded and ideas outside of my existing paradigm hit me. Suddenly, I could imagine a totally new path for myself, that I hadn’t considered before: instead of a startup, could I imagine actually working for someone? Having a family? Becoming an artist? Or working in the outdoors?
This appreciation of nothingness surely doesn’t come natural to me. I’m generally a goal-driven creature, always looking for purpose in whatever I do. Being busy makes me feel valued and gives me a sense of meaning. So maybe by labelling nothingness as productive after all, I found a way to play my mind a trick that allows me to just relax and enjoy the boredom.
In any case, gaining this perspective made me appreciate my transition even more, not just as dead time between two real engagements, but as a beautiful and valuable thing in itself. I recently talked to a musician friend about this and her analogy was: “great music is not just notes, but equally needs the pauses. It’s in those moments of silence when you feel the music the most”.
What have you learned about transitioning?
I’m just at the beginning of my life-long journey of understanding transitions and I’d love to start a conversation with others who are going through a transition right now or have gone through one in the past — and learn from each other. Are you in a transition right now? What have you learned from transitions in the past that will help you next time? I’d love to exchange notes and start a conversation, feel free to reach me via Twitter, Facebook orpforti@gmail.com.
Other recents post by Fabian: 3 Life Lessons From 11 Days Alone In Yosemite’s Wilderness
Thank you to Nico, Rahaf, Niamh and Kalsoom for giving feedback on an earlier version of this post!
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