Confessions of a Serial Job Hopper

#4: Ignore traditional career advice.

The fact that I’ve spent the past 31 years working on my own terms and have managed to make a good living shocks me. It’s even more surprising that I’m still going strong as a relative “dinosaur” in the tech field. In hindsight it would have been so much easier to take the traditional route: get good grades in high school, graduate from college, and settle into a cube for the next 40 years.

But that route seemed like death to me, so I did it the hard way.

I wanted to make money, and didn’t want to wait.

The average age for a CEO is 59. Who wants to wait until you’re almost old enough to collect Social Security to run the show? Why wait? I’m supposed to put in my time, pay my dues, and wait for someone to decide I’m good enough? Fuck that shit.

I was 100% bored with school and knew what it took to make it in the world: work hard and be better than everyone else. So I bought a bunch of books, hijacked time on a Unix terminal, and away I went.

I was developer without a college degree way before it was cool. The problem was no one would hire me, so I had to get pretty damn creative.

I would take a job, spend 6 to 12 months working there, picking up skills and making connections, then start looking again. I did this for about 5 years and racked up more experience across different domains that I ever would have if I had stayed with one job for those 5 years.

By the time I was 30 I was running my own company that grossed over $10 million a year. Me and my partners sold the company and walked away with a nice chunk of change that held us over until the next thing came along.

After the dust settled from the sale (and I’d satisfied the terms of my employment agreement), I went back to my old job hopping ways.

During every interview, someone would ask why I moved around so much. I told them the truth:

I like to get in, solve problems, and move on. I’m not a maintenance programmer, and I’m a horrible employee.

Good times, no shit. Why lie?

The people that were looking for long term commitments would thank me for my honesty and we’d usually part ways. The ones that were looking for solutions would work to strike a deal.

But that was way back when, right?

Surprisingly, even with the popularity of the “gig economy” there is still a negative view of those with a collection of short-tenure jobs in the past. I’d imagine the number one factor is the cost of recruiting and retention.

A company wants to hire good boys and girls that will shut up, sit down, and do their work. A least until such time that the company decides your services are no longer required.

Take your life back.

Lifelong commitments are for friends, family, and good dogs. Don’t trust the corporate bullshit for a second, because the second you stop making money for them you’re gone. To believe anything else is absolute fantasy.

Wake up.

The dirty little secret that everyone should know by now is that employers need us a lot more than we need them.

This is about you, and it is OK to be selfish when it comes to employment. It is your life, your time, your dreams, your money.

Nothing is free.

Haircuts, massages, bar in the basement, lunches, motivational speakers over lunch, happy hours, etc. It’s all business and just a trick to get more hours out of you.

Do your work, then go meet your friends for happy hour.

Job Hopping Tips

Tailor the resume to the job.

Clean your resume up and tailor it specifically for the job opening. Use keywords that are used in the job posting in your resume. Keep it clean and short and focused on the job.

Your resume is just a tool and the recruiter will spend about 10 seconds scanning it, they don’t want to read a story, they are scanning for keywords.

Skills to pay the bills.

Maintaining your skills in critical.

Figure out what you’re good at and then market those skills. Don’t think you have any marketable skills? You do, I guarantee it. My skills as a successful gambler, uh, I mean my hobby playing DFS and poker, applied directly to project management (risk management, reading people, financial management, scheduling).

Now I kick ass pulling multi-million dollar software projects out of the toilet.

Get out there and do your thing.

Always be looking.

It’s easy to become complacent, particularly if you are being paid well and enjoy the work environment. But things can change in an instant. Always have an iron or two in the fire in case you need to pull chocks ASAP.

Ignore traditional career advice.

No one in my personal life could keep up with where I worked. “Why does it matter?” would be my response.

I’m a computer programmer, a web developer, a software engineer, a product manager, a software project manager, whatever. I write code for people, I help programmers figure out what to do next, I convince stakeholders to keep funding disasters, etc. I sell shovels to gold diggers.

I’ve worked on some of the dumbest ideas in the business. No offense to the people that conceptualized this stuff, because they pitched it and someone funded it. We would show up for the design, build, deploy phase of the operation then hit the road once the system was in production. Maintenance programming. No thank you.

When you land somewhere that feels right, hang around.

And on those rare occasions where it’s all coming together, there is nothing wrong with taking a breather and hanging out for awhile. My big things are autonomy (I’m a horrible employee remember?) and the ability to take time off between projects.

Think about what is important to you and keep an eye out for when your conditions are met.

The Takeaway

The 30 Year and a Watch days are long over, but the industrial machine wants you to think it’s still a thing. Public schools and colleges are set up to feed huge employers that don’t really exist anymore.

Create a life living on your terms.

You only have one.

There will be bumps on the road, but they are there to make sure you’re paying attention. So stay focused on you, learn in demand skills, and get out there and do your thing.

An interested observer, and occasional contributor. I write about mindset, motivation, and making money —

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