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"Try, Try Again" is Terrible Advice

Steve Halam on Unsplash -
Open up to it

Two months shy of my 48th birthday, I finally did it.

I gave up.

I took twenty-five years of toil in the corporate world and I tossed it over my shoulder.

I had finally decided that I was going to stop trying.

It was the best decision I could've made.

If At First You Don't Succeed...

Coming out of college I wasn't necessarily shiftless, but I was damn sure driftless. I had no sense of meaningful purpose whatsoever about my impending career.

Naturally, I started selling cable TV door to door.

The money was surprisingly good. The work conditions were not. Knocking on people's doors unannounced, often after dark, is sketchy. At times it legitimately felt dangerous. But I had gotten this notion that working in sales was a "good career move". I tried it for a few years before deciding it wasn't, at least not for me.

I felt like I'd failed right out of the chute.


So I did what I'd always been taught to do growing up: try. With my career in sales a profound flop, I went into RJTSAM - random jobs to stay alive mode - for a few years. During this time I tried a bunch of jobs, which means I can say that I have been:

  • A courier

  • A dispatcher

  • A radio broadcast engineer

  • A financial services support rep

  • An administrative assistant

  • A "business process engineer", whatever that is

Many of those gigs were temporary jobs, so I only tried them on for a short while. But one of them finally turned into a full-time gig working as a "Jim-of-all-trades" in the Finance Department of a fast-growing company. It was a really fun place and I was getting to learn a ton, especially about big computer systems. I felt like I was part of something.

Until I got laid off. (Sometimes "fast-growing" turns into "fast-shrinking" very quickly.)

Try Again...

At the age of 28 I found myself with a business degree, several years of "experience", not much money, and no job. I ruefully moved in with family and started looking for work. Fortunately, it found me very quickly - and this time, it stuck.

Because we all thought the newly computerized world might come to an end when the clock struck midnight on January 1, 2000 (remember the Y2K Bug?), some folks at a big law firm in Boston thought it would be a good idea to hire a guy with my experience to help them upgrade their billing system.


Actually, it was.

I was really good at figuring out technology. But I was even better at the thing I really liked: helping everyone involved with the technology work together to get what they needed from it - and do so while still enjoying each other.

That surprising career twist launched me on a 22-year journey through multiple companies and roles. I used my skills in IT to continue getting more opportunities to work with my real superpower: creating better human relationships.

First as a manager and eventually as a senior executive, I was continually given more responsibility to make the most out of people. I was really good at it. I had a lot of success.

And I was very unhappy.

Try "Not Trying" Instead

For over 25 years I tried to be something. Most of the time, I tried to be what I thought I was supposed to be. Or what other people suggested I should be.

Sure, I was moving towards a better mix in my work - doing more mentoring, leading, and managing. But I was still stuck in someone else's organization, working to bring their vision to life instead of mine.

So I quit. In mid-2018 I walked into a manager's office for the last time in my life* and handed in my letter of resignation. I had no idea what I was going to do next, but I knew it was time to stop trying to be and do what others expected of me.

(* - I think.)

In the first year and a half of building my coaching practice, I was trying really hard. I tried to be like other coaches I'd seen and learned from. I tried to project the image that I thought customers would want to see. I tried to learn everything you could ever know as a coach. And it felt really hard. I worried that I didn't have a viable business, that I would fail and have to go back to my old career, the one I knew I had to leave for my own good.

Then it finally happened.

I stopped trying.

Now don't get me wrong. I still put in effort, sometimes a lot of it. I'm a new entrepreneur building a business, after all, and that involves hard work.

But I do not try to be something else anymore. I know who I am. I know what I'm really good at. And I know exactly how I want to serve others. All I need is to keep showing up as me, with what I already have, and trusting that there are plenty of people who I can help.

My best strategy these days is to "not try". And you know what else? Not only am I succeeding, as I often did in my first couple of career stages. But I'm also very happy. And I don't even have to try ...

What are you trying to be and do in your life today?

What would it feel like in those areas to not try?


Jim Young is a coach who helps people - mostly men - with their careers and personal lives. He also runs really fun workshops to help teams learn better relationship skills that support healthy interactions at work, as well as in their personal lives. In many instances, he helps them overcome 'trying' situations. : )

Actually, Jim's new career is a lot like his old career ... just without all the trying. Having finally found the elusive combination of success AND happiness for himself and seeing how amazing it is, Jim spends lots of his time helping people find the same thing for themselves!

When Jim's not doing all that coachy stuff, he's fixing up his old farmhouse, raising three superb teenagers, doing live improv comedy shows (in non-pandemic times), and generally looking to discover new & funny things about life.

You can try to reach him - pardon me - you can reach him at


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