#1: Taking the leap
Friday two weeks ago marked my last day as an employee; at least for the time being.
After almost six-and-a-half years in the cosy comfort of a steady income, I decided to take the leap and embark on the adventure of building a startup. Not alone, thankfully. But together with my good friend and former colleague Elliott.
Sure, you think. That’s cool and all. But why the need to share this with the world? After all, aren’t there enough great (and even more not-so-great) blog posts about aspiring founders and their journeys from corporate dystopia to #ramenlife out there?
Absolutely. But I promised myself to make writing an integral part of my entrepreneurial journey in an attempt to keep track of the ups and downs that lie ahead. Plus, it’s a great way to get the word out about what Elliott and I are building.
So expect this to become a more frequent exercise on my behalf as I’ll lay bare our learnings, wins, and failures; all while we’re (metaphorically) jumping off a cliff and assembling a plane on the way down.
This is blog post #1: Taking the leap.
Don’t get me wrong, I find writing extremely hard and fairly unenjoyable for the most part. And doing it both well and consistently is even harder. But I firmly believe that there is no better way to organise thoughts, explore new ideas, reflect on past experiences, and ponder the future than putting words down on paper.
Looking back, truly understanding the importance of writing is one of the many practical learnings from my 18 month-long stint at Atlassian. No other product organisation I have either worked in or heard about practices writing as religiously as the home of Jira (I know, Amazonians may disagree).
And while overwhelming in the beginning, I experienced first-hand how much a culture of public documentation improves collaboration, reduces the need for meetings, accelerates communication, and helps avoid misunderstandings. Especially in today’s remote world.
Oh, and it doesn’t (shouldn’t?) all have to be strictly professional. Atlassian’s internal instance of Confluence hosts thousands of blog posts about everything from new product launches and customer research to holiday write-ups and restaurant reviews to philosophical debates about strategy and — this is no joke — the cafeteria’s selection of cheese. So get ready for a few lighthearted updates as well. That is if I can muster the discipline to actually write them.
Those who know me may remember that this is not my first attempt at boarding the Pied Piper train. But it sure is the first time that I’m giving it my all. Side-hustling a new business seemed like a great idea at first and worked well while figuring out what problem we actually wanted to solve. But I’m neither smart nor determined enough to make split-brain and context-switching work long-term.
And while I always knew that the only way to succeed is to focus, the appeal of a steady salary combined with society’s general response to the idea of quitting a well-paid job certainly didn’t make things any easier. Until, put on the spot by Elliott, I sat down one day and truly pondered going full-time.
Elliott’s and my previous attempt at building a company had failed because we had realised (too late!) that we weren’t passionate enough about the problem space to give it our all. Plus, being on sponsored visas certainly complicated matters.
But this time was different. The visa issue was resolved and both of us were not only incredibly passionate about the problem at hand but also had enough conviction that there was something there. After all, we had spent more than six months immersing ourselves in customer research and validating core hypotheses via a scrappy MVP.
I drew up a simple list of pros and cons: Do what you love, be your own boss, learn some new things, possibly succeed (although statistically unlikely). No salary, no bonus, no stock options, no paid holidays, no brand halo. Oh damn. It was hard to ignore how much the obvious quantifiable risks outweighed the tangible upsides on paper. And so I did what all wise people do: I turned to Google in an attempt to better understand how other, equally cautious founders had rationalised their decision to quit a cushy job and give entrepreneurship a shot.
One of the blogs I came across in the internet’s depths of self-help literature talked about the idea of unimaginable future rewards. Aptly named “The Day You Decided to Take The Leap”, the post argued that while humans can easily forecast the concerns of making any leap, there is no way to predict the numerous rewards that await them on the other side.
When determining whether or not one takes a leap, there seem to be better reasons to not make that jump than to do so. After all, the justified mind is one that understands loss aversion — one that wouldn’t want to trade the comfort and safety of the present moment for an uncertain and rocky future.
However, by not making the leap, we inevitably decide to give up on all imaginable future rewards for a limited number of concerns or risks that we can predict and prepare for today; an inherently asymmetrical relationship between the anticipated pros and cons.
Now, I’m neither a believer in fate nor exceedingly optimistic but the post’s underlying notion struck a chord with me and appealed to my sense of adventure. The same sense that had led me to push beyond my comfort zone in the past. And all of it had somehow brought me to where I was that day. Not too shabby.
I crumpled up the list, put on my running shoes, and took the leap.
Wow! You’ve actually read this far. I’m flattered! Especially since I haven’t even mentioned what Elliott and I are working on.
A previous version of this post included an elaborate outline of our idea, how we had come up with it, and where we were at in terms of progress. However, I realised that this made things not only too long but also deviated from documenting my key learning for today:
Taking the leap is [generally] not some irrational act that is driven by the passions. When you understand the asymmetrical nature of manageable concerns vs. unimaginable benefits, taking the leap is no longer an emotional jump, but a logical next step toward the life you want to lead.
And so I’ll leave you with this much for today: try to remember the last time you used an online job board (e.g. Indeed or Seek) to apply for work outside the knowledge industry. If you can’t, count yourself lucky. If you can, I bet you good money that the experience was far from ideal.
Yet, millions of people rely on job boards every single day to find work, move up the ladder, and build a career. We’re on a mission to fix that.
And no, it’s not another “Uber for…” platform.
Till next time,
Jascha
