How do you know when it’s time to move on?
For the past four years I’ve been working on Maptia, with my two cofounders Dorothy and Dean.
We’ve had a unique and unconventional startup journey, but after four amazing years, and with the full support of Dorothy and Dean, I recently decided that I would take some time to recharge before moving on to new adventures — the first of which will be with the wonderful folks at Escape the City.
Maptia will always be a part of me and it has re-shaped my lens on the world. From our naive beginnings in Chile in 2012 to launching Maptia 2.0 in December 2014—I’m proud of what we created together and how we supported each other through the highs and lows along the way.
I also feel an overwhelming sense of gratitude for all I have gained from the last four years and will be staying actively involved as an advisor—as the community, stories and platform continue to evolve and inspire in the years to come.
I have been fortunate enough to spend the last few years working alongside two of the most amazing, thoughtful, talented and dedicated humans (cofounders) that anyone might wish for.
Through Maptia, we embarked on a mission to gather a beautiful, shared record of lives and experiences from every corner of the planet.
On any given day, we would be greeted by heartfelt emails from a reader discovering Maptia for the first time, or a talented photographer (usually emailing from up a mountain or deep in the Peruvian Amazon) expressing words of appreciation for our editorial support. Others would mention how grateful they were to us for putting Maptia out into the world. All encouraging us to keep forging ahead.
There were truly amazing highs and yet despite carrying a wholehearted conviction in Maptia’s mission, for me personally the past year has been punctuated by days of feeling disorientingly unfulfilled, like something important was slightly amiss but I couldn’t quite put my finger on it.
For a good period of time, I was certain that my own existential funk was clouding my judgement. As any startup founder will tell you, there are always going to be tough times, from weekly lows to deep soul crushing existential crises. That’s par for the course. Startups aren’t for the faint of heart and we had been through a lot together.
We had retrospectively thought of our startup journey as a series of chapters — from Naivety (Chile) through Chaos (Seattle), into Perspective (Morocco) and Uncertainty (Switzerland) — each chapter fluctuating from moments of crisis up to excited and passionately felt idealism. So with helpful encouragement from Dorothy and Dean for some time my self talk was along the lines of:
‘C’mon, keep your head up Jonny, you’ve all been through things before, you can bounce back. Get some fresh air. You’re insanely lucky to be working alongside these guys, we’re making great progress… etc.’
This cycle repeated itself for a while, to the point where I accepted it as being normal.
It often felt like being caught in uncertain seas and thrashed about on a tiny rowing boat and it gradually dawned on me that my primary reason for staying committed to working on Maptia was to avoid letting down my cofounders, rather than because it was the thing that got me excited to jump out of bed in the morning (my “ikagai” as the Japanese might say).
Our personal circumstances had definitely changed around the time I began to question myself.
One of the biggest changes was that I had met someone, and had moved to live with my girlfriend in London, so we were no longer working under the same roof. Although our daily checkins via Slack/Skype functioned well, working at home alone left me feeling cabin feverish and craving the physical presence of other creative people. And even though we were all freelancing two days per week, I also caught myself sometimes wishing for more of a financial buffer.
In addition, as a non-technical co-founder, I felt that my impact to the product itself was limited and perhaps less essential than that of Dorothy’s and Dean’s. I knew that this was mostly in my own head, there were always many valuable contributions to be made in my areas of community building and growth, but I still felt insecurities about my work not being as impactful.
On the surface, these seemed like completely surmountable road bumps — but on a broader level, I felt like I was stagnating, learning less, feeling less challenged and drifting further ashore from my usual optimistic, enthusiastic self.
When sharing the first 1,000 days of our startup journey, we had written ‘be like cockroaches’ and ‘do things the long hard stupid way’ as two lesson’s learned’… yet there I was, hypocritically suggesting that I throw in the towel and step out of the arena.
Worse though was the shame story I was creating for myself that went along the lines of:
‘You’ll be failing your duties as a co-founder, leaving them with even more work to do in your absence. They’re already stretched thin and here you are selfishly wanting to jump ship.’
If I’m honest, I have always tied a great deal of my identity and self-worth to being a Maptia cofounder and I get the sense that many founders feel the same way. I felt that quitting would make me somehow less worthy, not only in Dorothy and Dean’s eyes but also with friends, family and people I respected, including myself.
A few months ago, I headed back out to Morocco to get some time in the ocean and to work remotely from a new co-working spot in Taghazout, the coastal village where Dorothy, Dean and I spent almost a year working on Maptia during 2013 — and while I was out there, perhaps partly because of the extra distance, these feelings intensified themselves.
Paralysed with indecision, I sought advice from friends and mentors who offered a combination of thoughtful advice and kind reassurance, saying that they would of course be there to support me whatever the outcome.
I recalled briefly meeting the designer and author Elle Luna at a book signing the previous year and re-read through the signed copy of her book to find this:
“Must is different [from should]. Must is who we are, what we believe, and what we do when we are alone with our truest, most authentic self. Must is when we stop conforming to other people’s ideals and start connecting to our own.”
I later re-watched a remarkable TED talk by Ruth Chung, she talked about how the hard choices we face often aren’t choices between equally good options but rather:
“There is no best alternative. Instead of looking for reasons out there, we should be looking for reasons in here: Who am I to be? What we do in hard choices is very much up to each of us… people who don’t exercise their normative powers in hard choices are drifters. Drifters allow the world to write the story of their lives.” — Ruth Chung
Amidst this web of thoughts, I sought refuge in the Atlantic to mentally untangle. I’ve found that for me that regularly dipping myself in salt water works wonders for creating clarity, or at the very least, provides a welcome break from my own overactive monkey mind.
It did and I returned with sinuses full of salt water, but feeling that the decision had made me. It now felt clear and somehow inevitable.
Although I had obviously mentioned the existential lows and issues that I had been struggling with on several occasions, and although I knew that my decision to leave wouldn’t come as a shock to Dorothy and Dean — earlier that day they had both said how readily they would support me if I did decide to move on, and had encouraged me to find the courage to be honest with myself if I wasn’t enjoying contributing to Maptia any longer — I still struggled with the feeling that I would somehow be letting them down.
I sat by my laptop for some time, anxiously spinning my pen, making cups of tea and tapping my fingers on the keyboard to summon up the cahones to initiate the call.
We shared a long, thoughtful conversation, with many a generous and honest word spoken on both sides, as of course, like all young co-founders, we had also experienced our fair share of internal struggles over the years!
In the end, they did a better job of articulating how I had been feeling than I ever could. They said that as much as they would have loved me to continue contributing to Maptia, and although they acknowledged that the transition would be challenging for them, they also stressed that they fully supported my decision.
I closed my laptop, hands quite literally shaking with emotion, and knew that a chapter in my life was drawing to a close.
After the transition period and going for drinks together for a final farewell, I am now back in Taghazout hoping to escape the British weather and chase some waves. Wandering around, it’s fun to remember how for 11 months in 2013, the three of us were living as a happy-go-lucky startup family in the very apartment (now converted to surf camp!) that I was again staying in on this trip.
Seeing the old water pipe in the corner reminded me of a time that we came back after dinner, on only our second night here, to find that the apartment was flooding in 3 inches of water, calmly proceeding to clean it.
I grimaced recalling a moment when I accidentally fed everyone cockroach noodles (in my defense they had been breeding in the open dried pasta bag). I noticed the chairs we’d painted the backs of that had been foraged in the local scrapyard.
One morning in particular stands out. After our usual breakfast of scrambled egg stuffed into half-dirham breads (affectionately termed ‘egg-pockets’), Dean and Dorothy ran into the office and excitedly explained that the shutters in one of the rooms in our apartment, if almost entirely shut would let through a pinhole of light from below, projecting onto the white ceiling.
It was completely magical. We lay on the floor gazing up at the ceiling watching full technicolour waves lapping at the sand outside whilst locals or a herd of vocal goats would sporadically pass by.
Now, sitting here, typing this with a view through that same window, it feels like I’ve finally come full circle. Time has passed, the pinhole camera shutter has been replaced, but the memories from this place are still vivid.
Looking back on the past 4 years, I feel overwhelmingly grateful to all of the talented photographers, passionate storytellers, inspiring entrepreneurs and frankly insane adventurers who I’ve been lucky enough to correspond with; it has been a real pleasure to help share their stories with the world.
I won’t easily forget our time spent living in a handful of heart-achingly beautiful corners of the world, from the mountainous regions of Chile and Switzerland to the surf rich paradises of Bali and Morocco.
But more than anything I’m grateful for the experiences, lessons and memories that we shared on the startup adventure, to Dorothy and Dean for their generous spirits, unwavering dedication and just for being there through it all.
I have no doubt that they will continue to breathe life into Maptia and I look forward to watching it grow into a compelling and jaw-droppingly beautiful living archive of stories as the next chapter unfolds.
To close, I’m sharing a few reflections, not as any kind of universal advice but just as personal insights that have emerged over the last few months, partly in case they might be of use to anyone else struggling, but mostly to ensure that I don’t forget them myself!
I have learned that making space to reflect, seeking pockets of stillness, regardless of how busy we are or how many unfinished and urgent tasks there might be, is essential for me.
Taking time to zoom out the lens from the default perspective that we assume and then showing up to do the emotional labour and take an honest inventory of the situation is the only defence I know of against the relentless confabulation machine inside our heads.
As with happiness, I would argue that making a positive impact on the world is a side-benefit from doing work that fulfils you. Many people might disagree with this but I don’t believe that it’s enough to be working on a project that makes a positive impact. The two are often very related, but, for myself, I have discovered that the work itself must also challenge me; fuel my creative spirit and throw me into a state of flow where I forget my own existence, stretching my mind in previously unimagined directions so that it never again returns to its original proportions.
Scrawled onto the Escape the City chalkboard in London is this quote and it it resonates with me now more than ever:
“Don’t ask what the world needs. Ask what makes you come alive, and go do it. Because what the world needs is people who have come alive.”
I’m certain that there will be many more hard choices in the future as well as times when I’ll feel like I have failed or let people down who I care about.
As Brene Brown says, the only guarantee of ‘living life in the arena’ (referencing the Roosevelt’s quote) is that you’ll continue to get knocked down. But as she says:
“The process of regaining our emotional footing in the midst of struggle is where our courage is tested and our values are forged… Rising strong after a fall is how we cultivate wholeheartedness in our lives; it’s the process that teaches us the most about who we are.”
People often think that it takes a lot of courage to start a startup, and usually it does! But for us, it was a no brainer— as idealistic and recently graduated students with few responsibilities or ties, we had very little to lose and a generous $40k grant from the Chilean government. But facing up to how I was feeling four years down the line, and then deciding that I wanted to move on to something new and sharing that with my cofounders, was one of the hardest things I’ve ever done.
As a surfer I barely think twice before jumping out into waves that are breaking one or two times overhead, I’ve conditioned myself to accept that I’ll take a few on the head every so often, but that’s a small price to pay for being out in the ocean. Applying this mentality to the rest of life isn’t easy though!
I hope to learn to make more courageous choices. It’s the only way to escape the trap of living a life in default mode. After all what else can we really take credit for in life except for these occasional moments of vulnerability and courage—nearly every other measure of success for me feels like it can be assigned to some combination of fortunate circumstance and genetic disposition.
Our time on earth is finite. All we really have in life is our time. Choosing how to spend it is perhaps the only question that really matters. The final word goes to Annie Dillard:
Thanks for reading and here’s to the many more adventures in the future. Allons-y!
