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Michael DubakovFibery founder
Essays

Entrepreneur self-doubt and confidence (take both!)

May 21, 20215 min read

A decent company founder or business owner is always a bit mercurial. Founders normally have confidence that everything will work out, yet they are also not sure how exactly. In other words, an entrepreneur is decidedly doubting.

Confidence ☀️

Without being sure of dream venture success, getting down to business is almost impossible. Unbridled optimism, a sense of one’s own superiority based on virtually nothing, an inner voice telling “you’ve got it right,” iron self-confidence, the ability to quickly make intuitive decisions with little or no information—these are the necessary companions of an entrepreneur.

Those all are a necessary, good thing. How do you start doing something new without self-confidence? Without it, taking risks is hard, and it’s scary to follow the long-term entrepreneurship road full of potholes, trials and tribulations, sudden turns, and rickety bridges. Only a total optimist can convince themself that everything will be fine and we’ll get to our destination alive. Only a total optimist can be a successful entrepreneur.

If you start to deeply, rationally analyze an idea and its implementation, this weighted think-through will kill your project immediately. That’s why the analysis must be carried out quickly, decisively, and—this is paramount!—superficially. Focus on the crucial things:

  • Is there a market?
  • Any competitors out there?
  • What are the competitors’ blindsides?
  • What’s the main strength of your idea?
  • Is it possible to create a solution at all?

If nothing outrageously contradictory comes up at that stage, stop overthinking and feel free to start working. Why? Well, because no one knows where all this will get you!

Self-doubt ⛈

Without hesitation and doubt in your way to the goal (or even the goal itself), nothing works either. A person in business needs the kick of constant uncertainty. Are we doing the right things? Is there a better solution? How about a cozier niche in the market? Do we need a blockchain (no, nobody does!)? Should we try a new experiment?

Very often, entrepreneurs lack a scientific touch. A new business must experiment. As quickly as possible, as objectively as possible, striving for as high quality as possible. It increases the likelihood of success. Good experimenters are always uncertain about the results and full of self-doubt. They surely expect and hope for some particular output but must accept anything, positive or negative. Any result is precious data that will help set up the next test or—let’s be honest—put an end to the entire research topic.

Good entrepreneurship, just as good science, is all about being unsure of the outcome of an experiment. You need to come up with a hypothesis based on some gut feeling, bring it to the market asap, and collect information. I’m pretty skeptical about any results obtained before the product is on the market. Surveys, chit-chat with potential clients, prototypes, focus groups—all that works crappy. Long story short, drop the indirect methods, test your hypothesis directly—create a product/service and show it to the world. Go for the real challenge.

Doubt in every experiment helps to face reality more or less objectively. If the data shows that the experiment has failed, accept it and leave this dead horse alone. The most effective way here is to take another horse, this time without an extra leg or wings, and try to ride that. Sooner or later, your horse will gallop. Maybe you’ll need ten trials to get one lively horse. Perhaps, in the end, yours will be an elephant, not a horse. But sooner or later, an experiment will succeed (that’s the total optimist speaking).

Now, experiments come in all shapes and colors. Some deliver in a couple of days, the others need a couple of years. Mind you, it doesn’t affect the general principle. You should think of even several years of software development as an experiment with unexpected results. Don’t fancy waiting? Make sure you’ve got two or three other experiments in stock to think them through while the first one is running.

Are you having no doubts at all as to the outcomes of your very first experiment?

That only gives you one chance. You’ll probably spend too much time and money on polishing this one product. Too much time will be invested in secondary, insignificant stuff (like Aeron chairs, a rocking page 404, logo by Paul Rand (RIP), a large, neon sign on a skyscraper office building). A healthy amount of doubt leads to better decision-making. Being confident about the first experiment gives you no room to err. Because, like, you’re completely sure, no mistakes can be made.

Reality shows, though: one chance isn’t enough. Take more.