How to Choose the Right Path

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I want to use this edition to talk about something we don’t usually talk about: the path you’re on, how you choose it, and — most importantly — whether or not it is the right one.

Truthfully, this is something that applies in many ways, and it doesn’t only come up when you’re first starting off. It will occur multiple times throughout your career — even when you know you’re doing what you feel you’re built to do — but you’ll still have to make hard decisions as to which way to take yourself, the team, or your company.  

A woman I worked with a few years ago stated, “My family thinks I’m nuts, but I’m just going to do this thing.” What was she doing? Leaving a stable job in academics to start her own company. She put all of her chips on the table, pulled from her savings, took very little pay, and decided to ride that to an end she believes will pay off.  

Could she have had an easier path? Absolutely. With her career history, she could have her selection of highly comped roles…but she decided on something that felt right to her, and she was able to manage the pushback, dig into herself, and do what she needed to do. 

But it isn’t just her. It’s you — and it starts early. 

Whether you want to go to college or not. Business school or not. Take the job or not. Go for the bigger job or stay where you are. Build a company or not. Fund that company or not (and how). To leave a stable job for a bigger opportunity, to acquire a company, to shift a revenue model, to leave a spouse, or to ask someone to marry you. 

It really never ends, but the choices keep coming — and the stakes just keep getting higher. 

Big rewards often come with big risks, it’s true. But sometimes, big rewards come from skillful and thoughtful transitions, pivots, and expansions. We don’t talk about those quite as much, but they are equally bold and brilliant in their own way. 

I’ll break down one way I help people make these decisions, an example, and a little inside baseball on how the best and most effective decisions tend to happen. No one is as locked in as they sometimes feel or believe. Let’s take a look at how you move forward.