My biggest startup mistake: Thinking it would save me

Whenever someone asks me about my biggest mistakes from the past, I’m a “no regrets, everything had its meaning” kind of guy. But lately, as I’m back in the driver’s seat of building a product these days, I had a chance to reflect both for myself and with a co-founder of mine about what I’d say the biggest mistake has been for me over these years.

When I built Buffer, my previous company, as much as I loved working on the product, growing it, and making it successful, I had another hope with it. One that was much more hidden and unconscious and it’s only becoming clear to me now these last few months as Here is ramping up: That it would save me. That it would save me from all my worries, all the difficulty and ups, and downs of life. That if I had a thriving, winning startup at my hands, all my life problems would just go away.

It’s the kind of strange and difficult projection I’ve since run into in a number of other aspects of my life. Some things that I hoped would save me over the years were:

• a great romantic partner
• meditation
• fitness
• great friends
• money
• an amazing house

The list goes on.

Things I was projecting onto my startup

There are a number of things, as I reflected on this over the years, that I hoped my successful and thriving startup would help me with. A shortlist of it is this:

• Feeling loved and welcome: I’d hoped that if I just worked hard enough and the business got big and successful enough, I’d fill the hole of wanting to feel welcome and loved in the world. It was a way to combat the scary loneliness I so desperately didn’t want to experience and feel.
• Mattering and feeling worthy: If I could point to something big and successful that I had built and contributed to, there was a hope that it would finally satisfy the gnawing question of “Do I actually matter?”.
• Saving others: Driven from some of my wounds from childhood, I was hoping that having a successful business would help me save others, my family, our users from eternal doom. Just come along for the ride using this product and you’ll be saved!
• Becoming free: One of my biggest projections was that of becoming free. Of hoping that the business would unshackle me from all worldly authorities and demands that were placed on me day today. That somehow if I was successful and big I’d transcend these issues, rise above, and float on a cloud, freely until the day I died.

Listing these feels a bit childlike and embarrassing. But also painfully true. Although there were other, “healthier” things contributing and driving me, looking into the mirror and acknowledging that these were a big factor too seems important.

Turning to the inner process

These days, when I coach other founders, I feel glad that I can help them identify some of these shadow motivations. The good news is that once we lay these shadow motivations bare and shine some light on them, we can find some solutions to deal with them, that isn’t unconscious. There are powerful and helpful methods to be with our sense of unworthiness, loneliness, wish to be free, and urge to save others.

It can sting a lot when I sometimes harshly have to pop the bubble for them, that working twice as hard on their startup will nonetheless not help them with these aspects of themselves, even when they are billionaires. It can be a hard truth, and yet once allowed in, one that leads to a lot of aliveness and inner goodness.

Work that’s worth doing

The second good news after the chance to make these unconscious drivers conscious is that it doesn’t negate or undo our dream of doing powerful work in the world.

Each of us longs for a meaningful and powerful contribution to other people’s lives, it’s no different for a startup founder or CEO. Of course, that’s often at the heart of why we’re starting a business in the first place.

Each of us has a chance to stake out what the meaningful contribution is we’re looking for with our business or product. This I believe equips us twofold:

• First, we develop a laser-sharp focus around what it is that we long to see in the world: More aliveness in our customers, more freed up time for them to spend with their family. More ability to self-reflect and create space. Whatever direction your vision points to, you’ll feel reassured knowing what it is.
• Second, by defining work that’s worth doing you also define what it isn’t going to help you with: feel less lonely, feel more worthy, etc. Anytime you get caught in a loop of that, you can look to your vision and realize: “Of course I’m not getting this from my day-to-day work, that’s not the point of it! The point is to contribute to people’s lives and help them with X.”

The summary for me is this

The work on our startups won’t save us. But doing meaningful and powerful work is a fulfilling and important aspect of our lives worth pursuing. It’s just important to know that it won’t negate our desire for other important needs and experiences we’ve looped in together into our startup and business adventures.

Good luck out there! 😃