Living with uncertainty

Living with uncertainty is the default state for any founder. There's a paradox at play. The highest level of certainty you have is usually at the earliest stage of a startup. Your vision is clearest. You have answered the call of a glaring problem or deeply felt mission. No external factors have emerged yet to derail your plans.

Then you launch, build a team, and start spending and bringing in money. Everything gets thrown into a constant state of flux. Product development goes off track. New competitors emerge. Your team fails to gel. The board thinks you should move in a different direction.  The product or marketing message confuses customers. Metrics lag. These and a million other things happen. Usually at the same time. Problems cascade. Every day, another stone of uncertainty piles onto your chest.  

So you make more plans. You set goals. Create an OKR structure. Obsess over metrics. Look for patterns. Impose more process on your organization. Increase communication. Probe for deeper answers in your 1:1’s. Manage the board. Conduct user studies. Refine the vision. Each of these activities removes a little weight of the uncertainty. But the pile of stones still grows.

You learn to live with it. You do your best to align current decisions with future goals. But know that you can only control your actions in the present moment. You focus on the process. Detach yourself from the results. Celebrate wins only in the moment.

As you persist, patterns emerge. Successes become more predictable. Failures point to avoidable symptoms. But new questions arise. Larger problems and complexities challenge you. The cycle of uncertainty repeats.

All the way through the end, the uncertainty never goes away. I’ve sold two companies. Both times, the deal felt close to falling apart right up until the wires hit. Meanwhile, I continued to operate the business on two parallel timelines. In one universe, the deal would close. In the other, we'd remain independent.

The cognitive dissonance any founder experiences during this time is immense. Yet it's also familiar. After years of living in the fog, I'd grown accustomed to carrying the weight of two worlds. I'd learned not to obsess over outcomes. And instead to focus on the actions in front of me I could control.

The thing is, the opposite of uncertainty is monotony. It means knowing that exactly what you expect to happen will occur. You're guaranteed fewer lows, but also fewer highs. As uncomfortable as uncertainty is, its absence can make life boring.  

The best way to manage uncertainty is to approach it as a series of challenges. You ride the highs and lows. Focus on solving each riddle as it faces you. Be assured that once you do – or even before – a new problem will emerge and the cycle will repeat.

You can’t get addicted to the cycle. You might start to see challenges that don’t actually exist. You only need to be mindful that problems are always there. You won’t need to look too hard for them. They’ll find you.

This mindset doesn’t just apply to being a founder. It’s also a good approach to life. Life is never the straight line path you imagined when you were a kid. It's more like a game of chutes and ladders. Just as soon as you hit some incredible stroke of fortune, you'll come face to face with an epic setback. You constantly need to adjust. You take the good with the bad.

Uncertainty is everywhere. If you don’t feel it, you may have insulated yourself too much. At some point, it will catch up with you. The key is to be ready.

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