The Many Paths to Success

“...when people are given what appear to be multiple paths to success, they will try to retain all the paths as options, even though selecting one specific path would have guaranteed them the most success.”

The many paths to success / midjourney

A common affliction that often affects founders of new businesses. Entrepreneurs are natural born hedgers. They are hedging their bets in the hope of finding the best route to success. In doing so, at both a macro and micro level, the risk is of opening up to many paths, hedging too many bets and in doing so dissipating your energy; reducing the benefit of compounding. And ultimately as a result failing to achieve success due to a thousand cuts.

The belief starts with a visual of a clear end goal; you’re trying to get somewhere. The nature of business targets is there is usually multiple routes to get there. At this stage everyone is on the same page. The smart choice here is to evaluate the many paths, understand the risks as best you can, then place your bet and then accept the consequences. Sometimes you’ll win and sometimes you won’t, often due to events outside your control. But the evaluation of risk is a mechanism to whittle down the possible paths. By whittling down the paths you get to focus your energy in a directed way; more on that later.

What often happens is the opposite. And it is deeply reasonable. Which makes it deeply dangerous. Confronted with multiple paths to success and an uncertain view of risk, founders will often hedge numerous bets. They will decide that actually to get to Rome we could walk multiple paths, and as a result set multiple armies off on the different routes; hypothesising that in so doing, they increase their chances of arriving unscathed. The logic seems compelling. In practice it almost never happens. It doesn’t happen because your energy, best people and best resources are spread to thin. You end up losing the power of serendipity that is gained by going deep. In addition, less lateral connections are created, your knowledge compounds less. The consequence of all of this is that each of the multiple paths start to seem fruitless and unlikely to succeed. The lack of focussed energy has cost you.

By directing your energy on one path, you’ve accepted the inherent risks. You have accepted that you may have made the wrong call, but with all the information you had at the time you made the best decision you could. Now you can overwhelm the situation with your energy, best people and best resources. And in doing so go deep, create more lateral connections, invite luck and serendipity, drive the compounding of knowledge and resources. The result is you are likely to go much further down the path to Rome and much more likely to see the fruits of the journey.

It’s a strange paradox of the perception, but sometimes hedging your bets is just that, a hedging of bets. And in an entrepreneurial journey maybe the best path is the calculated one.

The one that likely takes your the furthest if the winds are in your sails.