How To Have an Unusual Career: Step 1

Everyone’s career is going to be different. Even so, we have an idea of what some kind of normal could or should be. In this post I’m going to talk about how to have an unusual career. Let’s start with:

Step 1: How to Have an Unusual Career

Wake up.

Seriously, that’s it. As long as you wake up (Step 1), get out of bed, and go work on something, you’ll have an unusual career.

Unusual career step 1: get out of bed

Seriously, though, what is a usual career? Go to school, get a good job, pay your bills, retire and live on a “fixed income,” die…?

For many people that is usual. But more and more things have changed. Getting a good job in the olden days meant keeping a good job until you retired. Maybe you would change jobs a couple of times during your career, but for the most part there was a thing called job security. With pensions, social security, affordable housing, and health care for the elderly, people could imagine a retirement of relative rest, peace, and enjoyment.

Now, though, pensions are gone.

Social security is still there, for now, even though most people don’t trust it will be there when they retire. Affordable housing is a pipedream right now (hopefully this is a bubble but multiple people in-the-know say it isn’t). Health care is one of the hottest debated topics of the recent past, and doesn’t seem to be very affordable.

Each of those four things have to do with our ability to pay for life. If they are getting worse, or aren’t changing from bad, we are left reconsidering the other part of the equation: how we earn money. The “get a (good) job” part.

Part 2: Feeling Like You Have an Unusual Career

I got an interesting message from someone recently… I’m going to edit the question to generalize it a little, and keep this person anonymous, but the heart of his message is intact (Note: this person’s first language is not English):

Hi Jason,

I hope you are doing well.

I have something running around my mind that stumbles me and I thought you’d be the best person to share with.

Since I started doing _______ work (basically, an unusual career) in 2019 and other online teaching, writing and content creation effort, I started to see many revenue and growth opportunities outside the 9-5 and I did my best to share it with friends and people I love around me but unfortunately very few people seem to relate. I was only able to convince a single person [to follow my path].

The issue I am facing right now is that I started to feel that I am out of sync with my close friends. They currently have a highly focused career thinking and struggle to understand or see the potential of the online world (note: they are ALL in the IT) and find it hard to see [an unusual career] as a source of trustworthy business.

Besides that, I feel bad that their huge potential is locked to full time jobs. I started to feel alienated and not having people in the same frequency spectrum to share and discuss with.

I started to think to introduce new friends with similar way of thinking, but with my limited time it will be in the expense of the current dear ones. Frankly speaking, it feels for me selfish and materialistic just to think about friendship from this dimension, but I still need similar minded people to grow and learn.

What are your thoughts and suggestions around this?

Thank you so much,

– Dude who is doing an unusual career

Ah, my friend. Welcome to my world.

For those who don’t know, I got laid off in 2006 and, with the exception of a 10 month “real job,” I’ve been self-employed since then. Most of that felt like unemployed, for various reasons.

I still have people who scratch their head and say, “what do you do for a living?” (I do a lot of things, one of which is help job seekers organize their job search)


To say that I’ve had an unusual career is an understatement. I’ve been immensely blessed, and lucky (ahem). I’ve also prepared, and been prepared, for opportunities.

If you were to dig into my business and say, “WOW! How successful!”, you would likely ignore many, many years of preparation and failure. Years of rejection and losses, only to try again. Try harder, or try something different. And, at my side has been my wife of more than 25 years who has had to live with an entrepreneur for more than half of our marriage.

I think entrepreneurs have some illness without a name that basically is having an overabundance of optimism, perhaps to an unhealthy degree.

Part 3: What Is Normal?

For most of our children’s lives they have been homeschooled. Thank goodness homeschooling has less bad stigma now than it did in the 1900s, but there are still people who cringe when they hear we homeschool. “What about their social interactions?” “What about math?” “Did you go to college to learn how to teach kids?”

We’ve been unusual for a long time. We have chosen to be unusual. It was intentional. We didn’t choose to be the brunt of jokes, or the talk of gossips, but we chose a different path.

This path has become more popular, or more common, but it’s still not usual, or normal.

For years I’d hear my kids’ friends say, “YOU HAVE TO COME TO MY SCHOOL! IT IS SO MUUUUUUCH FUUUUUUUUUUUN!

Unusual career is not an easy path

Then my kids would say, “Why can’t I go to that elementary school down the road? It is so much fun, and Sally wants me to sit by her, and we can be best friends all day long!”

Um, no, sorry. If you go to that school you won’t sit by Sally, and there’s a good chance you won’t see her. She will likely even ignore when you see her because she is with her small friend group, and small friend groups in school are usually not open to outsiders.

Being normal, and going to Sally’s school, is not going to be the High School Musical you hope it will be.

And so we figured out, as intentional parents, why we homeschool. What are the core reasons? And are those core reasons accomplished at home, instead of at school? There are other factors that go into this, but my main point is (1) we were intentional about a personal choice, and (2) we chose the hard path (hard socially, also hard because it put more of the work on my wife’s shoulders).

This is not the first unusual thing we’ve done. We go to church, and are in a minority religion. I don’t like to talk about that on this blog because (a) it doesn’t matter, and (b) it still doesn’t matter. My point is, we have chosen to be intentional about our religion. It would be a lot easier to just say “we are ______,” and choose one of the handful of socially acceptable religions, but we didn’t. Rest assured that we’ve heard comments and have been discriminated against because our religion is not one of the mainstream religions.

We have chosen it, and it is not normal.

Back to my career: it is not normal. I can’t say “I work for XYZ company with ABC title.” That would be a lot easier for friends, family, and neighbors to understand. Instead, I’ve chosen a really weird path. A path with no commuting. A path without a steady paycheck. A path with a different choice of benefits, such as retirement planning (401k stuff), vacation (what is my sick/holiday policy), work hours (I left the “butts-in-seats” mentality years ago, swapping it out for “you eat what you kill). It’ unusual, and people don’t understand it.

My heavens, I’ve been married for over 25 years and have 5 kids. That is UNUSUAL.

unusual career unusual marriage but intentional choices

My career choice (or the career that’s has been dumped on my lap) is just one unusual thing of many. Not that I love being different, but I do love being intentional, and making my own choices, instead of doing the normal thing.

And with that, this blog post is long enough. Monday I’ll share my thoughts to my friend’s questions about having unusual career.