When should you quit your startup?

When I was about 8 years old, my dad used to take me and my brother out on his boat. It was a small craft, but I thought it was amazing.

One day, we were almost capsized by a passing luxury cabin cruiser. Looking up, I saw a man lounging on the deck being served champagne by his staff — basically he looked like James Bond. I knew immediately I wanted to be like that guy with the much cooler boat.

Over the years, that image stayed with me. When my family hit financial challenges and I was told to study hard so I can be better off, I thought of that guy. For some strange reason I decided that he must have been some sort of businessman, and even though I had no idea what that actually entailed, I had to become one as well.

Fast forward to 2013, a time when being the founder of a tech startup was one of the coolest-sounding things a millennial could do. The idea of being your own boss is inherently attractive … but you also get to build cool stuff, geek out, work with people you like (or at least with like-minded people), set your own schedule, challenge the status quo, and possibly MAKE MILLIONS. It’s a very attractive proposition, especially when you’ve been burnt out by a job market in which most companies have no idea how to engage their people.

So this “formula” eventually took shape at the back of my mind:

Found a startup + Do cool stuff + Sell the company + Buy luxury boat = Achievement Unlocked!

A few years ago, on a weekend trip to Italy with a friend, we decided to start a business empire together. It was one of those mad plans which typically get hatched around great food and wine, but unlike most other ideas born in such circumstances, this one actually took shape into a real company.

Our idea took shape, supported by the incentives and mechanisms that are now in place to encourage the creation of high growth startups. Based on pure potential, for years we breathlessly delivered consulting & training projects, identified a market to disrupt, built a team, set up partnerships, released a product, changed direction, organised events, dealt with the emergence of competitors, started building another product, and raised tens of thousands in grant funding from various Maltese and EU institutions. For a long time, I adored everything we were doing, and even in the low points, at least I was learning more about myself than I ever had before.

And yet, a few weeks ago, I resigned. I didn’t decide to do it overnight. I had been struggling with the decision for over a year, and even now that I’ve made the move, I still question it sometimes.

I mean, how can you know it’s the right time to quit your business — or anything, for that matter? (That’s why you’re reading this right?)

The reality is that you can never know for sure. Just like the decision to start a business is hopefully based on a calculated risk, the decision to move on has to be as well.

If you’re like most people, you’ve probably been in a situation (a job, a relationship, a degree program) which you knew you needed to quit but just couldn’t bring yourself to. That’s because human brains are wired to seek familiarity. When you’ve spent years giving something all of your energy and attention, quitting is nigh impossible without torturing yourself for ages first. This is what known as the commitment fallacy.

The scary thing is that it’s hard to recognise this feeling for what it really is. The disillusionment doesn’t kick in all at once, but slowly seeps in, while you try desperately to ignore it and justify staying with arguments of job security.

The truly resilient entrepreneur, however, knows that one of the most foundational leaks in any business is doing the wrong kind of work, so they prioritize doing the hard “emotional labour” (in Seth Godin’s words) to create their own personal definition of success — not one based on what they’ve unconsciously absorbed throughout their lives.

Knowing what you really want — and being honest with yourself about it — is the first critical step for any entrepreneur who wants to succeed on their own terms. It ensures the alignment of personal values and goals with those of the business you’re building. It also allows you to move on if something isn’t a good fit any longer.

I’m not saying give up quickly at the first sign of trouble — quite the opposite. Following through on my startup dream helped put me closer to an understanding of who I am and who I’m not. It’s crucial to give a project your 100% effort — after all, at some point, you must have thought it’s the right thing do. At the same time, allow yourself the luxury of being clear-eyed enough to realise when, after trying your hardest, it’s simply not working anymore.

If you can’t come to a final decision or act on your decision alone, open up to your loved ones or mentors. I’ve been extremely lucky in finding a lot of support in a time of painful transition, but I had to reach out first. I worked with a coach, spoke at length with various mentors, and even sought advice within online communities from other entrepreneurs who had moved on from their initial ventures. Also, remember that if you’re not in the venture alone, communication is key. I spoke to my business partners, at length about our ambitions, and that allowed us to part on good terms.

While I did not make a decision in a vacuum, I did have to spend hours in introspection and journaling, to figure out that my original childhood dream was naive and idealistic, absorbed through the culture of success, and that it wasn’t what I really craved. Knowing my MBTI personality type (ENFP) also helped in this process, as it allowed me to understand my tendencies and to map out who I’m more likely to become based on my real strenghts.

Observing kids in a playground, you will notice that when a game isn’t working, they find another game to play. Yet by the time we reach adulthood, most of us have lost touch with what they truly want. We have a self knowledge crisis, and it’s leading millions to stay in situations that simply aren’t working.

Yet if I had to speak to that 8 year old child today, I would not try and make him see that he’s fixating on someone else’s dream for him. That’s a process that anyone has to go through on their own time. The best way to find out if your dream is worth pursuing is by doing just that. Just be aware that there is a very real possibility that you will discover that it wasn’t really your dream to begin with. If that happens, have the courage to admit it to yourself, and seek support to move past it. See that disappointment as bringing you a step closer to figuring out who you’re truly meant to be, then redirect your energy into a different cause, project, or work that appeals more to your sense of self.

At its core, it’s that simple.