Reflections from a gunshy social entrepreneur
Aug 26, 2026
I was obsessed with WeFlex for 10 years before it even started, it was my ‘reason for being’ and my ‘singular mission in life’, then at 35 I left it.
So. What do you do when your ‘singular mission in life’ is behind you, but most of your working life is ahead of you?
Moreover, how can I go and promote my new company and ventures when for years I was talking like that about my old company?! It felt like inviting someone to my second wedding and recycling my old vowels. I won’t lie, I felt self-conscious about it, and I still do.
This is an odd dynamic that I feel is unique to social entrepreneurs, because as personal brands ourselves, we get tied to our social enterprises’ missions and serve as a mascot as much as a professional. Seeing the Colonel do anything but sell fried chicken would be weird, and so it can be for some of us. For a while I wondered if that meant I had used up all my currency and goodwill, like I only get to play the ‘this is my passion’ card once, and I’d already spent it.
Honestly I was pretty depressed for a while, felt adrift and battled with meaning and existential attachment. For the first time in years I had to meet myself outside of my career and reconcile (and also get a full night's sleep). After wondering about if I made a mistake walking away from the magic I created, I realised that I created the magic.
Yet, there’s an overwhelming sense of gunshyness now in my career, a timidness where once there was only unabashed audacity. Which makes me a hypocrite, considering that I preach fervour and confidence to aspiring social entrepreneurs who I now coach and support.
I’ve found new passions and interests, and realised that there is no true ‘existential fulfillment’ from a job, there’s only cool ways to spend your time and make your money. The second time around is much more fun and there’s less pressure to save the world, which is nice.
So cheers to a more public career, it might be awkward and it’s definitely nerve-wracking but I’ve done tougher things. This article is the start.
I’m not done yet.
TT
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