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Change your life. It’s never too late.

How to make a personal pivot


I’ve pivoted so many times that if my personal and professional journey had an investor, they would have replaced me with a seasoned CEO and forced me out of my own life.

My girlfriend Emily Dunn wrote a blog post over the weekend. It’s definitely worth checking out.

Here’s why I’ll never be a lawyer

I loved it as soon as I read it. She’s writing about the choice she made after she graduated from law school and landed her first job in a firm. That choice was to walk away from the career path she’d been focused on for the past 4–5 years. It was a choice to accept that her journey was right, while her destination was wrong.

That’s a hard thing to admit. I think there are thousands of people who never manage it, who set themselves on a path and never work up the courage to change lanes when they find themselves locked in an unhappy situation. These are the people who reach 40–50 years old and are suddenly in crisis because they feel like life has passed them by and left them behind, and they don’t know what to do.

Making a pivot in your career is tough. Making a pivot in your career can feel like a major setback, and it can make you think that your time has been wasted. But it can also save your life.

When I talk to people, when I get up and give advice about how to grow a business, or how to find customers, or what to do when you’ve built a company you love and sold it for chump change because you’re a f—ing idiot (well done, 19 year old Jon) I think they have this idea that my entire life is a linear progression that’s taken me to this point.

That’s patently untrue. After I explore some of what I’ve done, the reaction is always total surprise. I tell people that in the past 10 years, I’ve started multiple businesses, made money, lost money, screwed people over and learned most of the plays in the book. And that’s what they expect to hear. But then I tell them I’ve toured full time in a band, had and lost a record deal, dropped out of law school and worked on a top 10 album, flipped burgers and designed a porn website for a guy I’m 90% sure was a Russian mobster.

My “career” is pretty much a series of unfortunate events, incompetently tied together and arranged in no logical order with no logical end goal. It’s been driven by my need to build, and create, and make things, and be independent — but it’s not a story that makes sense.

I’ve pivoted so many times that if my personal and professional journey had an investor, they would have replaced me with a seasoned CEO and forced me out of my own life.

And you know what? I’ve got a lot to show for it. A lot of debt that I’ve had to work off, a nuked wasteland of failed businesses, a huge box of CDs that were never sold, some pretty shady contacts and about 50 years’ worth of hard lessons crammed into 10 years. That last one is what’s made it all worthwhile.

I guess the biggest realization I’ve had is that you can always learn more — and it’s never too late. If you’re unhappy with where you’re going, take the next exit and go someplace else. If you think your career is s— and you studied the wrong major at college and you hate your job, do a reset. It’s got nothing to do with going back to the drawing board. You’re just taking the time to learn.

Today, I help people develop as entrepreneurs, creatives and innovators. Is that the natural progression from the past 10 years of my life? No. But it’s informed by the lessons I learned.


One of my favorite books ever is the Pursuit of Happyness. A man who has lived and breathed a series of bad career choices risks everything he’s got to change lanes and change his life. This quote has stayed with me for a long time:

“Others may question your credentials, your papers, your degrees. Others may look for all kinds of ways to diminish your worth. But what is inside you no one can take from you or tarnish. This is your worth, who you really are, your degree that can go with you wherever you go, that you bring with you the moment you come into a room, that can’t be manipulated or shaken. Without that sense of self, no amount of paper, no pedigree, and no credentials can make you legit. No matter what, you have to feel legit inside first.”

Don’t be scared to pivot. There’s no age limit to it, you don’t have to be old enough or young enough, and there’s no rulebook to follow. When you find yourself at a point where refusing to quit means committing to a life you’re only going to hate more and more as the years go by, you do have a choice. You always have a choice. And a pivot means you’ll keep moving forward.

If you enjoyed reading, please support my work by hitting that little green heart!


Jon Westenberg has appeared and published in Business Insider, Inc.com, TIME and dozens of other publications, talking about startup entrepreneurship, writing and innovation. Jon has helped hundreds of businesses worldwide grow their audience and take control of their future. Jon is an investor, an entrepreneur and a dreamer.

Jon Westenberg is on a mission

Originally published at medium.com

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