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"My Career Feels Unstable. Should I Have Done Something More Traditional?"

Don't look back. But look forward a little differently.

Welcome to One Thing Better. Each week, the editor in chief of Entrepreneur magazine (that's me) shares one way to be successful and satisfied at work — and build a career or company you love.

This is a preview of my first newsletter for Premium members.

Today’s reader question: “Am I stuck?”

Made with DALL-E

Vanessa writes:

Being part of a startup is the hardest thing I've ever done, but also the most exciting. Change feels like a constant — the highs are HIGH and the lows are low. I truly love what I do but sometimes find myself questioning the risk and wondering if I should've taken a more traditional career path. How do I square that?”

My answer:

Vanessa, you’re really asking a question about control. You love your work, but you don’t feel like you control enough of your life. And you’re wondering if you can ever have both — the satisfaction of a non-traditional path, and a life that’s steady enough to enjoy what you’ve earned.

But I also think you’re asking the wrong question. So I’ll help you ask the right one, then offer an answer. (Spoiler: Yes, you can have what you want... but it takes a different kind of work.)

To start, let’s back up and talk about hard work — and the trade-off it demands.

Why we do what we do.

I began my career in journalism, where a colleague once told me this: “If you can do anything else, go do that.”

They weren’t trying to be discouraging. They were showing me the keys to an exclusive club. The message was: “There are easier, less stressful paths. You didn’t choose them, because they wouldn’t have satisfied you. You are choosing a hard path because you’re compelled to — because it is the price you’ll pay to do what you love.”

I liked that. It felt like a badge of honor. And as my career evolved, I realized that this thinking isn’t exclusive to journalism. Many people, in many fields, say this of themselves — and in your startup world, I’m sure you relate.

But let’s be honest: You didn’t sign up for the Suffering Olympics. You don’t want hardness to be the measure of your professional worth. That gets old — especially as we get older.

So here’s the thing to know: Hardness and satisfaction don’t have to be a package deal. But to decouple them, you’ll need to start making intentional choices. You’ll need to choose the level of hardness you want, and define what satisfaction looks like.

Here’s a question worth asking yourself:

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