The keys for me for job satisfaction are now pretty basic:

Is my manager supportive and someone I like spending time with?
Is the work continuously interesting? Will I develop skills that are likely to bring interesting opportunities in the future?
Is there incentive alignment between what I offer and what the company needs?

This blog post will attempt to describe my thoughts on what makes for a fulfilling career. It’s a hard question. Maybe something in here is valuable as you search for your “ideal” career.

Likely useless career advice

Now for a stream of consciousness about corporate employment…

Some say a job should help you 1) earn or 2) learn and if neither then leave. But that framework doesn’t really work because you can learn anything anywhere.

Knowledge is accretive. As I look back on jobs I didn’t love, I still learned things. I wasn’t a fan of the type of consulting I was doing 10 years ago, but I’ve now started a consulting firm and having had that experience is helpful. So it’s all kind of gray. I didn’t like pulling weeds as a kid but I’m now pulling weeds as a homeowner so yea, I’m glad I know how to do that.

what is life anyway?

Per Guide to Decision Making, “resulting” may apply if you say you made a good decision because you enjoyed a job. By the same token you made a bad decision because you didn’t enjoy the job.

The reality is that “all or nothing thinking” is more of a cognitive bias, per The Coddling of the American Mind and The Worry Cure. And so, you’re going to learn things as long as you’re remotely interested in learning things. Whether they satisfy your Working Genius is another matter.

I want my “dream” job though

Can you land your dream job? Or is it a myth? 30-40% of first time marriages end in divorce. And not all of the remaining 70-60% are blissfully happy either. But many of those 70% ARE blissfully happy. Or they will be. Or they were and they will be again maybe or something…

Marriage and work are similar: they’re a type of relationship.

Happiness in a relationship takes both people being committed to the happiness of the other. One sided relationships eventually crumble. But if both people remain committed to the other’s happiness, and other certain caveats…, the marriage will prove valuable to both for their whole lives.

Professional and Life happiness

Happiness to me comes in two forms: doing the best I can with the circumstances I have (the cards I’ve been dealt) and choosing environments that are healthy (the game that gives me the cards).

It’s about 1) what you’re doing and 2) the environment and context you’re doing it in.

This is life. Some games are fun to me. Others less fun by definition. But any game may be better than no game. Unless the game involves a high risk of me breaking my spine. Nuance.

Point is: it takes a long while to find what environments you thrive in. Any company can offer just one or potentially many environments depending on their size or the role.

So if you don’t know what you’re interested in, you must explore. You try.

Finding the best environment

First on the environment.

Jane Austen is better at this than me. Take all those sisters in Pride and Prejudice who have varying views on love and stability. Some sisters believe in true love. Others think it’s a myth and instead choose financial stability. Of course true love wins in the end.

I suppose work is very similar: you’re going to get out of it what you believe is possible. After all: you work with and for people.

It will take time and risks to figure out what environments you thrive in, kind of like dating. The interview is part of the process. Bring in a company is another part. Talking to friends in other companies is a third part. Thinking grass is greener is a fourth part, and so forth. That’s life.

Your needs also change in your career. As you change, your preferences change. It’s up to you to learn how to match your preferences with your environments, and how to accommodate your preferences within your environments.

If you don’t like your roommate, you can leave early or wait till your contract expires or etc etc. or you can try to work it out and get to know your roommate. All are options. Which you choose is up to you. In the end, a good environment takes two. But it also takes one to instigate change for the better for both. Reciprocity.

Experiment Your Way to a Happy Career

Then there’s the thing you’re doing.

You can “try” anything by doing it yourself. Do you want to be a teacher? Go try to volunteer teaching. Do you want to be a coder? Spend 20 hours trying to build an app. Do you want to be a doctor? Volunteer with doctors.

Four ways of learning what you like emerge. The quality of the information is ordered top to bottom while the amount of time it takes to get that information is bottom to top:

Reading about an industry or job is kind of helpful.
Talking to people in the field is more helpful.
Following and shadowing those people is even more useful.
But actually doing the work is the only way to really know.

You can read about 50 jobs to see what piques your interest and help you learn what’s out there. Next, you can increase the chance of pursuing a job you like by trying to do it without actually having to get the job.

You can get a pretty good sense by doing little projects similar to what the real work is going to be.

Don’t Not Try Something Because of a Dumb Reason

A lot of people think they shouldn’t do something because they’re not good enough. Even professionals. (Tiger Woods just had his worst round of his life, but I’m guessing he’s still better than you.)

Or they think they shouldn’t try something because they’re not yet credentialed. “Don’t try this at home kids”. It’s what we’re taught.

And that’s kind of the great myth: the myth of titles and credentials. That you need to be experienced at something to be able to do that thing. But that’s a lie. Instead, you should only pursue the credential if it offers you something you can’t otherwise get (due to red tape). And until you get the credential, you’re just spending a few hours every day learning stuff and maybe passing an exam at the end. So if you ignore the exam, what’s stopping you from just picking up the activities today you may find rewarding?

I once spent a single week shadowing dentists in an open room in Honduras. I was a Spanish translator for these American dentists that came through. I felt pretty confident by the end that I could probably do one of the fillings just because it really wasn’t that complicated. And the dentists told me so. Once you look at 100 cavities in a mouth it’s not hard to spot them. This was the easiest way to de-myth this job: watching and observing.

It was actually really boring. Once you’ve seen 100 cavities you’ve seen them all I think. Glad I figured that out quickly! But I know there’s someone out there that disagrees with me and I’m glad they’ll be drilling my teeth and not me.

90% of most people’s jobs could be taught via apprenticeship, like the good old days. Today’s world of credentials makes people think they’re incapable of doing a pretty simple task: putting a tool into someone’s tooth. But before you invest 8 years of your life in dental school, why not go be a dental hygienist for 1 year? Instead of doing a coding bootcamp, why not just code in your basement for a month after hours? This is the way to find what you like.

Whether you enjoy doing that thing that created value for people can only be discovered by doing it.

People Hire you Because you offer a Service or Value. Period.

Your real job is to create value for people. It’s not a title. It’s not a credential. It’s not mandated or necessary in society. And if you were born 100 years before today or 100 years after the job may not exist. So think about opportunities in this way.

A healthier way to thinking about corporate life is: what creates value? Is there a reasonable exchange of goods for my offering?

I’m capable of many offerings. But they’re hiring for one offering. That’s life.

If I were selling apricots, and someone was offering me peanuts, would I exchange my apricots for their peanuts? Well, if we were the only two people sure.

But maybe I feel like I can get some avocados for my apricots. So can I find an avocado dealer? Do they even like apricots? Do they already have enough apricots? And if yes to all the above, are they even in the mood to exchange for apricots today? Lastly, do they like me?

Getting a job is more of a negotiation than anything. And everything in work is a negotiation. Read Never Split the Difference and that becomes quite apparent. Work is nothing fancy. It’s not a title. It’s not a degree. It’s just doing little activities.

And after you’ve 1000 similar activities you’re soon labeled a data scientist or a farmer. And if you circled the right boxes on an exam and got a piece of paper you’re now a doctor/dentist. But the paper or the title don’t make you good at that thing. My point: create value, not titles.

In Sum

So yes. I’ve gone on a rant here. But hey this is my blog. I’m trying to talk about the deeper issues at how to choose a profession or a company within that profession. I’m trying to break away from the titles and credentials that blind our thinking away from the more important questions of “what activities bring me joy” and “how will I know it?” And “will someone pay me for doing this activity?” And “how do I find an environment of people that will enable me to do valuable activities and make it a pleasant place to work?” (PS, some say to not work for Elon Musk…unless you enjoy his working style.)

Long story short: make sure the company hiring you actually needs your skills to run their business. Strive to find better opportunities by putting yourself out there and trying new things. And find people you like working with. All the rest is just a bonus.

The most dangerous thing is to get all those good things on your first job because then you try to self actualize per Maslov’s hierarchy of needs. “Don’t it always seem to go That you don’t know what you got ’til it’s gone?” (Lyrics) So if you get a “bad” job just know it’s part of the process and one day 10 years from now you’ll probably be grateful you had that job anyway.

If I didn’t actually answer your questions that’s because some questions are a perennial debate. Some popular people hate the idea of work-life balance, some embrace it. Go figure. And keep searching to find someone who sees work and career the same way you do, because there are millions of jobs in the work. Hundreds of millions.

Books to read

It helps to get perspective when choosing where you want to work.

How to Decide: Simple Tools for Making Better Choices - have a decision framework
The 6 Types of Working Genius - understand who you are.
Overcoming the Five Dysfunctions of a Team - it helps to recognize a good company by first understanding a bad company.
The Old Man and the Sea - a job is a job at the end of the day. It’s just fishing.

Practical Questions

Things I’d think about in your shoes:

what loosely sounds interesting? Who perhaps knows someone with that type of role? How do I get 15 min with that person, or a quick email? (Use 6 degrees of separation to your advantage)
do I have an ideal salary? What’s realistic? (Levels.fyi, don’t over or undersell yourself. Figure out market rates and if your job will support your desired lifestyle in a location)
what’s the entry level job that gets me some experience 50% in the right direction that I’m interested in?
where will I learn?
Does this company offer flexibility to try new things?

Sometimes job searching is helped by thinking by contrast:

what can someone not pay me $500k per year to do? $300k? $100k? (Nobody could pay me $500k to be an investment banker and work 100 hour weeks. Maybe they could pay me $2M and I’d do it for 2 years ya know? But $500 isn’t enough.)

As you’re interviewing:

what incentivizes people on a daily basis?
will this job be around in 2 years? Why? Why not? Why might they fire me in 6 months for things 100% outside of my control? (Recessions, business strategy shifts, etc)
how essential is my skillset to what they do?
what relationship do people have with my would-be manager?

Questions to potentially ask your hiring manager:

How do you see me fitting into this role?
Why might this role not be a good fit for me?
Who’s the highest ranking person who’s quit or been fired recently and why?
How do you define success for this role?

Questions to ask your peers you’re interviewing with:

describe your relationship with your manager?
describe the communication patterns of the team?
describe how decisions are made? What’s a recent decision that was made? describe your role in how the team made that decision?

Other thoughts:

Writing a Tech Resume

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Bryan lives somewhere at the intersection of faith, fatherhood, and futurism and writes about tech, books, Christianity, gratitude, and whatever’s on his mind. If you liked reading, perhaps you’ll also like subscribing: