By Guest commentary Tuesday, September 8th, 2026

By Josh Damigo

Two years ago, I became the president and CEO of an organization — my first true “big boy job.” Three days later, I was told I was not a “cultural fit.” That sentence still stings to write. I felt like such an idiot. 

There is something uniquely disorienting about having your professional identity change twice in the same week. (Walking in with a new decorative poinsettia only to walk out with it in a pretty much empty cardboard box.)

Two years later, I’m still finding my footing.

For ambitious professionals, work has an interesting way of becoming part of how we explain ourselves. Think about the famous networking question: “What do you do?” When your career is going well, the answer flows off your lips like a song you’ve known since grade school. 

It can become a vanity mirror we use to remind ourselves why we matter. 

Do you know who I think I am? When something disrupts that story, the answer suddenly becomes much harder to spit out. 

Shortly after losing that job, my life became a Rascal Flatts song: I lost my job, lost my girl, lost my car. I ain’t gettin’ ’em back, no matter how much pedal steel I add.

We all love a good comeback story. Someone loses a job, reflects, works hard, discovers their true calling and six months later is happier, richer, posting photos from keynote stages, has somehow lost 4% body fat, grown more hair and now refers to getting fired as — say it with me — “the best thing that ever happened to me.” 

That hasn’t been my experience. Applications go nowhere. Interviews go really well, but I’m “overqualified.” 

Consulting work comes and goes. Coaching clients are sparse. Networking meetings somehow lead to MLM offers and pyramid schemes. Eventually, a particularly nasty thought sneaks in: Maybe they were right. Maybe I’m not a cultural fit.

That’s about the time you need one of the most difficult four-letter words in the English language: help. 

Last week, I publicly told my LinkedIn network that I’m looking for my next professional opportunity. I enjoyed approximately 0.006% of the process. 

I’m much more comfortable being the person offering help than the person asking for it, and I suspect many business leaders feel the same way. We build our careers around being capable, resourceful and dependable. 

Life hands us a problem we cannot solve ourselves, and suddenly asking for help feels less like resourcefulness and more like standing on the corner asking for alms.

The responses to my post were fascinating. Some people sent opportunities that had almost nothing to do with my background or what I had actually asked for. They clearly read the headline, but not the article. Others pointed me toward paid resources. Thanks. 

Some people in my field reached out with introductions, ideas and conversations. A few asked why I didn’t simply work harder at building my own business because I was “too talented” not to. And some people did something surprisingly helpful: They asked me for coffee and actually listened.

Then came the networking mixers. There is something uniquely humbling about discussing your employment status while wearing a sticker name badge that is ruining your “needs a dry clean soon” suit and drinking a flat glass of eight-year-old wine donated by the “generous” wine sponsor. 

Those conversations made me ask an uncomfortable question: Was I like this when I was employed? When someone asked me for help, did I actually listen to what they needed or did I immediately start throwing solutions at them because I wanted to feel helpful? 

It also applies to asking for help. “I’m looking for a job” is easy to say, but it isn’t very useful. 

“Do you know anyone in learning and development, organizational development, leadership training or a related fieldwho might need someone with my experience?” is harder to choke out, but it gives someone something to do. That requires humility, courage and remembering something I lost sight of after those three days: A career is not one title. 

Losing that role did not erase the people I had trained, the clients I had helped, the teams I had led, the programs I had built or the lessons I had learned. My competence hadn’t disappeared. My relationships — the good ones — were still intact. My experience may have had a giant thorn in it, but there was still a lot of rose left.

When professional momentum gets interrupted, it is easy to confuse “I don’t currently have the role I want” with “I am no longer valuable.” Those are not the same statement. 

One is a circumstance; the other is a judgment. Ambitious people can be remarkably cruel to themselves when they confuse the two. I’m still looking for the right next opportunity.

One lesson keeps returning: We tell emerging professionals to find mentors, build networks and ask for help, then many of us spend the rest of our careers trying to look like we no longer need any of those things. That’s backwards. 

Maybe asking for help isn’t evidence that we’ve stopped being capable. Maybe it is exactly what capable people do when they finally understand the limits of doing everything alone. It has taken longer than I expected to find my footing again, but I’m finding it — and this time, I’m much less interested in pretending I got here by myself. Plus, it’s their loss. 

Idiots.

Josh Damigo is the founder and consultant of Ambitious Adulting 101 in Ventura County.