5 Career Truths Your Boss Won't Tell You

Your résumé gap isn't a flex. It's a career death sentence

Someone posted on X, bragging about resume gaps as if they were a status symbol: “Do employers actually care about ‘gaps in your resume’? Like can’t you just be like, ‘Yeah, I decided not to work for a year’ as a flex?”

The answer is absolutely Yes, employers do care. It’s critical to avoid gaps in your résumé. This is one of the many lessons, sometimes painful, that I’ve learned about careers over the years, some from personal experience, others from watching what happened to others.

Here are five things men, and women, need to know.

1. A lengthy gap in your résumé will make you unemployable.

A friend of mine once turned down a lower-paying tech job after a layoff. "I don’t want to take a step backwards" he told me. Some months later, he couldn't even get interviews for call center positions. His skills hadn't changed. His experience hadn't vanished. But that gap in his résumé had made him radioactive to employers.

Beware the résumé gap. I’m not talking about taking a gap year when you are young. After you’ve clearly transitioned into full time work, an extended gap in your résumé will make it very difficult to get a job. If there’s a big gap on your résumé, it won’t even make past the automated screening companies use today.

I used to say that any employment gap longer than a year would make you all but unemployable. Today that gap might even be less.

This happened to multiple people I know, not just my one friend above. Being in this situation is utterly terrifying.

The people I know were only able to get jobs by begging people in their network to bail them out, which ultimately happened. If you don’t have people in your network like that, you could end up in real trouble.

2. Solo bootstrapping a startup is a very high risk endeavor

Bootstrapping is attempting to build a startup without taking outside capital. It was hot for a while a decade or more ago because it was heavily touted by the people at the company now known as Basecamp.

I’ve seldom seen the bootstrapping approach go well. I actually did it myself for an urban data analytics platform called Telestrian. I successfully built it. In fact, I still use it for my own work. It even had revenues. But it never really took off. I did not have either the financial or personnel resources to make it grow and eventually shut it down.

Bootstrapping only works where you get to cash flow positive extremely quickly. Nick Huber, known as the “sweaty startup” guy on X, is a strong advocate of only starting businesses that generate cash within a few weeks. If you are starting a prosaic business like power washing or some other home service, then this is possible. If you are trying to build a software company, forget it. Venture capitalist Marc Andreesen says raising money is the easiest thing an entrepreneur has to do in building a business. So why not raise some and do it properly?

Not only is bootstrapping a risky endeavor, it may not even be seen as a real job by a prospective employer if it fails. One of the people I mentioned who ended up with a résumé gap that made him unemployable got that way by doing a bootstrap startup that for whatever reason was not seen as real self-employment. If you set up a real company with outside funding, this won’t be a problem.

If you are going to bootstrap, at least start it as a side hustle until you get some real market traction.

3. It’s much harder to change careers than commonly believed.

You’ll sometimes see people say things like, “The average person has seven different careers over the course of their life.” Don’t believe it.

People tend switch careers at two main times. One is when they are earlier in their career. You are in your mid-20s, you can often switch to a different industry or role easily. After age 30 or so, this gets much, much harder. The other time is in late career, when people downshift, either voluntarily or involuntarily.

A former Accenture colleague did a study of what around 30 of our former colleagues were doing. Almost all of them were still in the same basic line of work 20 years on from when we were working together.

Switching careers often requires doing things like going back to school. One of the biggest reasons people get an MBA is to make a career pivot. That’s two years and a lot of money out of pocket. Wanting to go into fields like law, architecture, etc. means extensive schooling. One person I know who did switch from Accenture style consulting into architecture took six years to pull it off.

People making a career switch often have to take a step backwards in their career to do so. That’s also painful.

I personally switched careers from consulting to public policy research and journalism. Had I realized how difficult that was going to be to pull off, I never would have even attempted it. Even shifting from writing about cities to cultural issues took years to become a sustainable enterprise. To be blunt, most people have almost no chance of pulling something like this off. It’s just too hard and uncertain.

We look around and see people like Mitt Romney, who bounced around from private equity to running the Olympics to politics and think this sort of thing is normal. But this is rare, limited to people with very unique talents, connections, and resources.

Don’t underestimate how difficult it can be to make a true career switch.

4. Your network is critical

Everyone nods along when they hear "it's not what you know, it's who you know." Then they go back to sending résumés into corporate black holes.

Most people just take whatever relationships emerge organically. They don’t actively work on their network.

You have to be intentional about creating and maintaining connections. The best way to do that is making sure you are someone who is adding value to your connections. You have to give to get.

Not every connection is the same. It’s well known that so-called “weak ties” of people you know but aren’t close to are often the most beneficial in finding jobs or other opportunities. But strong ties matter too. When things really go south - say you end up like those people I know who weren’t able to find work anywhere because of a gap in their résumé - strong ties are the people who are willing to go to bat or even sacrifice for you. That’s worth its weight in gold.

Once you have a network, you have to remember to use it. You can’t expect people in your network to know that there’s something you need from them. You have to make a direct ask.

You Have to Be Willing to Make the Direct, Audacious Ask

5. The war for talent is bunk

"We can't find good people!" Every CEO interview, every earnings call, every industry panel - they're all singing the same song about the talent shortage. It's compelling theater.

It’s also bunk. Employers are still holding the cards in hiring.

I lived through a real talent shortage situation during the dotcom boom. Want to know what that looked like? My employer was giving out huge raises of 30% or more in “market adjustments.” My own salary almost doubled overnight. I’m not seeing anything like that today.

Companies have a vested interest in complaining about the difficulty in recruiting, because that lets them lobby for favorable government treatment and policies, such as more H-1B visas.

Reality tells a different story. Many people who get laid off have trouble finding a new job. Every job posted online gets a large number of applicants. Companies reject people for being “overqualified.”

After the recent online debate about working for Panda Express, I looked up their manager salaries where I live. A LinkedIn job posting for an assistant manager position there had already racked up over 100 applications.

Yes, if you're in the top 1% of your field - the AI expert who built one of the first LLM models, the sales leader who's never missed a quota - you're in demand. But that’s not most people.

Never overestimate how much leverage you think you have in the job market, at least not today’s job market.

The Truth About Mentoring

If you liked this post, be sure check out my two part series on mentoring.