Feeling Stuck in Your Career? Take it From Steve Jobs: It Gets Better

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Are you feeling lost or directionless in your career? Like you’re on the wrong track or you’re wasting your time?

I can assure you you’re not alone. Practically everyone has felt that way at some point in his or her life.

I can also assure you that it’s going to be okay.

Take it From Steve Jobs

steve jobs

photo credit: James Mitchell via photopin cc

If you don’t believe me, let’s go to the one source that’s cited on every subject under the sun, from creativity to leadership: Steve Jobs.

He had something really smart to say on planning your future:

“[Y]ou can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something—your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”

Trust in Something

So maybe you hate your job. Or you feel you’re not living up to your potential. Or you think you’ve reached a dead end—a new venture didn’t pan out like you expected or you didn’t get that promotion you wanted.

It is not the end of the world. And it hasn’t been a waste of time. It’s all leading to something, whether you know it or not.

I’ve seen countless examples of this among my friends and colleagues. Like the college graduate who felt stuck in an admin job for two years. But the connections she made there helped her get into a top law school.

Or the dissatisfied ad agency account executive who eventually used her hard-earned marketing skills to build a successful (and more fulfilling) career as an artist.

And I’ve experienced it in my own eclectic career.

I Dreamed of Being a Famous Actor

For most of my life I pursued a conventional career in business, doing corporate communications and PR work. But for the longest time I felt I was destined for something more creative.

So about 10 years ago, I signed up for classes at Chicago’s famed Second City training center, birthplace of comedy legends from John Belushi to Tina Fey.

Over several years I took hundreds of hours of classes in improvisational comedy, acting and sketch writing and performed in more than a dozen student shows. I then advanced to comic and dramatic theater, getting cast in the very first play I ever auditioned for.

Finally, I remember the day I got signed by a talent agent. My feet were three feet off the ground. I left an excited message for a friend: “I’m on my way!”

Soon I was doing national commercials. Old friends from across the country got in touch to say they’d seen me on TV. It was intoxicating.

I was still doing my “day job,” working with corporate clients on their communication issues, but acting had become my true passion.

Then My Dream Was Crushed

But there comes that time in every actor’s career where you realize just how stacked the odds are against you. For me it started with the dismissive remark of an instructor who said, “Rob won’t make it—he’s too old.”

That was devastating. And it was just the first of several such signals about my true destiny as an actor—the opportunity that passes you by, the mentor who lets you down, the “big break” that goes nowhere. Not to mention the many thousands of highly talented and experienced actors who are barely eking out a living themselves.

Eventually I had to ask myself if it was all worth it. The thousands of hours and dollars spent, the sacrificed relationships, the important life events missed. Yes, the experience was fulfilling, but was it all just leading to nothing?

A Funny Thing Happened on the Way to Fame

Then I figured out a few things. I found that I was feeling more creative in the business side of my life. I was doing better, more inspired work for my clients.

And I saw how the worlds of acting and business were connected. They both require you to engage with an audience, to express yourself creatively, to tell stories.

That revelation led to a book, and then to another book and then to a burgeoning speaking career.

And now I’ve found a way to combine the thing I love (performing on stage) with all the business knowledge I’ve accumulated. And in the course of that, I’m actually helping other people to communicate more effectively and make their way in the world more confidently.

It’s incredibly satisfying, and it was utterly unpredictable.

Connecting the Dots

When I first stepped foot into Second City, books and speaking and workshops were the farthest thing from my mind. But when I look back on it, it all seems like a completely natural progression. In fact, I couldn’t have planned it better if I tried.

I call it “strategy by hindsight”—the way things seem to work themselves out.

But it’s not just happenstance. Something inside, on an unconscious level, is leading us in a certain direction. Our gut instinct is outsmarting and overriding our brains, moving us toward a goal we can’t yet envision.

It Gets Better

So if you’re feeling stuck or lost or like you’re not getting anywhere, trust that it will lead to something.

You may not be able to “connect the dots” now, as Steve Jobs said, or see how it could possibly benefit your personal or professional development, but no experience is a total waste of time.

Even if it teaches you what you don’t want, that’s a vital step in learning what you do want.

So hold on. Relax. Breathe. Trust.

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Rob Biesenbach
Rob Biesenbach is an independent corporate communications pro, an actor, author and public speaker. He's fighting to end dull, ordinary communications in our time. He also has a mailing list, which you can sign up for here in full faith that he will not violate your trust.
Rob Biesenbach
Rob Biesenbach


  1. says

    Great post Rob thank you, after a disappointing new business failure this comes with open arms. Your perspective is giving me fuel to trust my gut in branching myself out in a new direction for the purpose of learning a new skill, although at first it felt like "there you changing your mind again" now I see it as a piece of my puzzle that is missing for the bigger picture (my dream). My dream is not dead it's just not happening at this time.

    "Connecting the dots as I now believe this could be."

    • says

      Thank you so much for sharing your story! Learning to trust my instincts has been one of the hardest things for me—I'm so used to processing and analyzing things. But very often, the gut does know better. Best wishes with the new direction!

  2. ushakr2014 says

    This has helped so much! And it does take courage and quietening to listen to that voice within. I am also given to exploring in different directions and this reassures me that nothing goes waste. Thanks! Usha

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