Daniel Vassallo @dvassallo had been quite a force on Twitter. He recently shared how over the past year he’s been doing what I had aspired to do during Opportune October – random daily schedule, only driven by what needs to be done, what he feels like doing, and what opportunities he seeing before him. 

So I asked him, what advice would he give, what tips does he have, for folks like me who’s trying to set up life that way? And guess what? He said—in effect—go find a job. Following the barbell strategy from Nassim Taleb’s Antifragile, he suggested to find a low-stress gig that pays the bills but leaves you with spare time and energy. Use said time and energy to do whatever I want, without being answerable to anyone or any ill consequences. Basically, it’s hard to settle into doing your own thing if you’re trying hard to even survive. And that’s so true! I’d been trying to get to a better place financially due to COVID, but all the while trying to get to that perfect place where I can pursue opportunity with ease. 

It’s not about going for broke or staying on in unhappiness. The whole point is to avoid false binaries like that, and have a ‘mixed portfolio’ of risks that doesn’t cause total ruin nor lead to total disillusionment. That’s the barbell strategy.

Does that mean I should go get a job now? Hmm nope.

I had better paying gigs before. Things like my design consultancy. I think I should not look back at my past in distaste, even if I’m trying to transit out of it, but with maturity and stewardship of someone who’s wants his new career as an indie maker so bad, that he’s willing to do what it takes to keep going, even if it means taking a few steps back. 

Barbells for the win.