Not failing > succeeding

I’m feeling stuck bootstrapping my SaaS and other current projects. Not sure if it’s due to my slump, but fact is, growth on Lifelog had been slow. My other products are like Carrd plugins and keto list directory are also stalling. It’s been 1-2 years. The data speaks for itself, whether my mood reflects it or not.

My products aren’t performing as well as I wished. I was hoping at least 1 product would have had promising results in my portfolio of small bets, but nope.

The success I seek isn’t quite panning out.

But reading Daniel Vassallo’s thread made me realise perhaps going for success is the wrong approach. Simply not failing is better.

He explains it well (reproduced word for word here, for my own reference. Emphasis my own):

Why bootstrapping is riskier than you think:

When I quit my 9-5 job, my plan was to bootstrap my own SaaS business. I wanted to identify my ideal business opportunity, and try to make a living out of it. And if that didn’t work, I was going to look for the 2nd best opportunity, and give that a shot. And so on.

The idea was to do things in series until something worked. This sounded very reasonable at the time, but that feeling didn’t last long.

The problem was uncertainty. How much time should I give until I declare something a failure and move on to the next? And what exactly is failure? What if something was succeeding slowly? And what if a more interesting opportunity emerged while I was still trying something else?

While I had a decent runway to experiment, it wasn’t infinite. And time was ticking. Then, about 6 months in, I had an epiphany. I realized that in this early phase, I shouldn’t be trying to find the ideal opportunity.

Instead, I should first try to make my self-employment arrangement sustainable. I needed to stack the odds in my favor and do my best so that this lifestyle doesn’t get taken away from me. The rest became secondary.

This idea changed my perspective. What I started caring about wasn’t succeeding, but not failing. I simply didn’t want to go back to a 9-5 job.

More specifically, my new strategy was to find a few small wins: opportunities with a quick payoff that required very little upfront cost, effort, or lead time — even if that meant that they weren’t the most enjoyable and had very limited upside.

Then I’d try as many of these small bets as I could, and run them almost in parallel. I would keep what works, and throw away the rest.

I had never saw it that way before. This is despite having followed Daniel and his approach for over 1 year, and having built a portfolio myself.

I had always assumed “a portfolio of small bets” is about launching a bunch of products I enjoy working on in order to find the ideal business opportunity that would in turn lead me to the success I want – that is, to disconnect time, location and creative autonomy from money.

But I realise now that’s actually stage 2. There’s something more fundamental before that peachy aspiration.

Stage 1 is: Don’t ‘die’. Don’t fail. To me, failure = going back to 9-to-5. Survive being self-employed at all costs.

Not failing > succeeding

Or better yet, be a cockroach:

If you want to make in self-employment, don’t think of yourself as a founder, a CEO, an innovator, or an entrepreneur.

No. You must think of yourself as a cockroach, trying to survive. You want to avoid having this lifestyle taken away from you.

– @dvassallo

It’s more about removing chances in order to avoid my worst case scenario, than increasing chances to achieve my best case scenario. At least when starting out.

Prevent downsides first. The upsides will come once you got the downsides managed.

Survive, then thrive:

“To thrive, you must first survive. The order matters. Once survival stops being a pressing concern, go for some more ambitious opportunities. Mix different income streams to tame uncertainty, and when some bets start paying off, eliminate those that are least enjoyable. As soon as you can afford it, optimize for enjoyment. Otherwise, none of this will last!”

The other insight I got from this is I’ve always avoided unenjoyable projects on this path, because it’s about being aligned to my lifestyle. But perhaps like Daniel said, it’s not so bad if the time/effort is capped. You don’t lose as much if you can drop it anytime. A few days to a week of commitment is not soul-crushing (limited downsides).

I want to see what happens when I try launching low cost, effort-capped small bets even if they weren’t the most enjoyable things.

Cockroach > unicorn
Not failing > succeeding
Survive > thrive