My battle with ‘Post Founder Depression’

Part 1 of 3 in a series about my life after a failed startup

Back in May this year, my journey as a founder effectively came to an end. I’d spent 2 years building Ping, until it finally ran out of cash and we couldn’t raise any further capital. And in parallel my own health deteriorated to the point I couldn’t effectively continue the work at hand.

In the 6 months since then, I’ve taken the time to invest back in myself, try heal some of the physical, mental and emotional wounds of the endeavour, and get myself back to work. I’ve been lucky to find good chunks of consulting work to keep me fed and watered whilst I took time to work out my future — the big old question of what’s next?

The reality is, this question has been even more complex than I anticipated, and has contributed significantly to volatility in my mental health. It’s surfaced thoughts, emotions and feelings about me and my identity I’ve never explored at real depth. It’s important to reinforce at this point, that this is not a moan or complaint about my situation, especially as I actually consider it one of immense privilege.

This is intended to be a deeply honest and open account of my experience of life at this inflection point in my career, acknowledging that despite there being a fair share of writing out there telling people about what to expect of life as a founder, there is very little detailing what to expect when you are one no longer.

The futile search for a ‘Carl shaped role’

I’m proud and consider myself lucky to be a generalist. I’ve worked in design, product, marketing, brand, community, partnerships, business development and much more, and consider the diversity of this experience my education and preparation for life as an early stage founder.

But having been spoiled in a role that allows me to turn my hand and creativity to a wide range of disparate problems, I now find myself incapable of finding one that exploits the true breadth of my capability. Every time I see a job description or have a conversation, all I see is a utilisation of barely 10% of my possible contribution.

The fallacy of Generalism ≥ Craft

Generalism means, at least in my world view, that there are plenty of ways I can create real value for the businesses I work with and for. Sadly I don’t think that’s a world view shared by the broader world of work — placing much greater weight on those with a craft (or what is perceived to be craft at least).

The reality is, I know my craft is brand. It’s been the primary driving force behind every single role in my career without ever having brand in my job title. Alas, that’s not what people see on a CV (no matter how much you might try and make it tell that story).

The societal dilution of ‘Founder Stock’

I remember when I first set out to build Ping, I had a lot of people say to me ‘regardless of whether it works, your personal stock will rise as a result of having the guts to have a go. You’ll walk into any job you want’. Sounded great despite the fact I believed I was going to be building Ping for the rest of my life.

Being brutally honest, I don’t think I’ve had a single conversation or interview where people are interested or care about my time as a founder. I may as well have been just out of work for 2 years, as they focus their energy and questioning on my corporate career.

Without significant rounds of venture funding under my belt and 50+ employees to account for, I do ask myself whether I ever really built a company? As access to the tools to and education to build and create are increasingly democratised, it’s actually never been easier to start something and ‘be a founder’.

I really didn’t want to be a founder. I didn’t want to ‘work on a startup’. I wanted to build a mammoth, impactful company. Frustratingly, your motivations and intent isn’t what people really care about — it’s ultimately what you’ve achieved by society’s standards.

The sunk costs of a ten year career

Last month was my ten year anniversary of entering the world of work after university. That’s ten years of being a brand builder in and around the world of technology. I’ve built a reputation, a network and a portfolio of work that would allow me to continue building that career till I’m old and grey.

But what if I didn’t? The beauty of a blank canvas is exactly that. When nothing is sure, anything is possible. As I’ve spent time trying to better understand where I get my energy, what I am really passionate about, what I could spend the rest of my life doing, it doesn’t always point towards brand and tech. I’ve certainly had a few ideas, but am I prepared to give up what I’ve built to pursue something radically new?

The incurable bite of the founder bug

Once you’ve taken an idea and turned it into something tangible and real, there really is no better feeling in the world. And knowing something it was not just used but loved by other humans, that is something that will live with me for a long time. Knowing you can build and create whatever you can fathom is a universe of possibility that it is, ironically, impossible to leave.

That said, the deep personal sacrifice required to build something from nothing hangs over you. I’ve learnt my lesson here for sure. I know I have little interest in building a venture backed company as a founder again, but a sustainable, slow-and-steady, revenue-generating business? Never say never.

The tangled headphone wires of intrinsic and extrinsic motivations

The seemingly relatively pedestrian question I asked myself was ‘Do I want to work for someone else again, having now worked for myself’? This question led to some pretty deep exploration of self, to understand the motivations for why I wouldn’t want to work for someone else again.

Turns out all my reasons for not wanting to work for someone again were deeply rooted in extrinsic motivations. I don’t think my career has been devoid of intrinsic motivation — it is what has given me confidence and ambition to build a better life fo myself. Sadly, I can’t deny that chasing fame, recognition, praise and money has all been in the mix too.

Trying to remove those motivations from decision making is bloody hard, simply because they’re so embedded in both our conscious and subconscious. It’s for that reason, for the first time in my life, the notion of ‘trusting your gut’ (which I’ve lived by for as long as I can remember) has been challenged. This is one part of my personal reality that has been hardest to address.

So what now?

I don’t feel like any of these above questions, thoughts or ideas have answers. I’m ok acknowledging that fact, but that doesn’t make it any more comfortable to live with. This time has been made all the more excruciating by the fact I’d as good as been offered a dream Brand job not too long ago, that felt so right in light of all the above, yet the role was deemed surplus to requirements at the 11th hour.

Since that day everything has been thrown up in the air, and the feelings of inadequacy and the lack of purpose and direction have come flooding back to destabilise my life. It’s been a real wrestle, but despite the absence of the things I need in my work, such as certainty, a sense of contribution, and the variety of creative stimulus needed to keep me fresh, one thing is very much present. An ongoing, deeply uncomfortable path of personal growth that’s given me the opportunity to look at my life in far more detail than I’d ever anticipated being able to.

I cover one of the more transformational and important parts of that journey in the second post in this series — my work is no longer my identity — where I attempt to identify my most intrinsic motivations and shape up a new life moving forward.