The 10 Types of Side Hustlers

No two people are alike. We all have different circumstances and motivations that shape our behavior.

My reasons for pursuing side income streams may be different than yours. In fact, over the years I have picked different jobs for different reasons.

The following are ten different types of side hustlers. Take a look and tell me if any of these people sound familiar.

Escape Artist

The escape artist hates their job and is looking for a way out.  Maybe they’re burnt out.  Maybe they regret their career path.  All they know is they are looking for the nearest exit.  There is nothing wrong with being an escape artist, but there are risks involved.  These hustlers are the most likely to leap before they look.  In their rush to get out of Dodge, they may take the first decent job that comes their way.

arrow communication direction display
Always identify the nearest exit in case of a career emergency.

Escape artists often suffer from the grass is greener syndrome.  As a result, they spend a lot of time changing lawns.


Bored side hustlers feel stuck in a rut and want something new that excites them. They may pick a side job that is drastically different than their day to day life. For them the paycheck is almost an afterthought.

Tired of your monotonous admin job Monday through Friday? You need some clinical time to rekindle the fire.


Manic hustlers can’t stand sitting still.  They need to fill every day on the calendar. Some people have hobbies rock climbing, painting or reading. These people have chosen a different hobby – work.

It may seem crazy, but these people enjoy working and get antsy when they have nothing to do.

FIRE Chasers

Want a surefire path to financial independence? Get a high paying job (or a few) and invest most of your money. Get a side hustle and take the live on none challenge. These disciplined hustlers have their eye on the prize. They aren’t pursuing passions. They’re pursuing cold hard cash they can stockpile.

photograph of a burning fire
More fuel for the FIRE

Alimony + Audis

There is nothing sadder than a high earner living paycheck to paycheck. You may think it is impossible to spend $300,000 a year, but some people manage to do it.

A wiser person might see the error of their ways and try to cut their expenses. These hustlers have a different solution: just work more.

photo of audi parked near trees
Some people trade in cars and spouses every 3 years for a newer model.

Unfortunately, if you can’t live within your means on $300,000 you probably can’t live within your means on $350,000. The side hustle income ends up doing more harm than good because now these people’s lifestyle inflates and it is difficult to cut back work hours.

Single Parent

Daycare ain’t cheap and 529s don’t fund themselves. It’s hard enough to raise kids when you have someone to helping you, but single parenting is a whole new world. Single parents don’t have the luxury of someone else’s paycheck coming in.

Empty Nester

After years of fantasizing about having more “me time”, empty nester hustlers don’t know what to do with themselves. They suddenly have more free time than they know what to do with.

They can explore lower paying jobs now that their bills are lower and there are less people depending on them. Maybe they are thinking about quitting their main job but want to test drive some side gigs before taking the leap.

close up photography of bird nest
Empty nests are quiet.  A little too quiet.

Ladder Climber

Ladder climbers see side hustles as a means to an end.  They specifically target jobs to get credentials or experience. They may use a part time gig just to get their foot in the door.

Don’t stand in the way of these determined hustlers. They will keep climbing the rungs whether you like it or not.

branches bright buildings clouds
Climb those hustle rungs to the top

Specific Goal Saver

All good things come to an end. Some hustles are meant to be temporary. Want to buy your next car in cash? Work a locums shift once a month for the next year. Trying to pay off your student loans in a hurry? Bust your hump until you make that last payment.

It’s OK if you don’t enjoy hustling for hustle’s sake. Sometimes you just need to muscle through a necessary evil.

Money Addicts

Money is addictive. Even if you don’t have an appetite for material possessions, money can mean many things. Freedom, options, power, respect…they all have a price.

There’s a reason billionaires continue to work. At a certain point it just becomes a fun challenge to see how much you can earn. If you walked by a $100 bill on the ground would you pick it up? This is how money addicted hustlers see the world: the streets are lined with $100 bills that everyone else is stepping over.

“Enough” is an illusion

Which Type Are You?

I’ve been several of these over the years. If I’m being honest with myself, I’m part manic, part FIRE chaser and part money addict. Early in my career I was a specific goal saver and locums shifts got me the down payment for my house.

Whatever your motivations, I hope you find a hustle that meets your needs.

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8 thoughts on “The 10 Types of Side Hustlers

  1. I probably am in the Escape Artist camp myself, although I am pretty cautious and do look before I leap. I won’t kill the Golden goose (my primary gig) until I am well in the range of FI already. Another subtype you might consider is Passion Seeker. Although it may be already under the purview of the Boredom one. For me, it was not because I was bored/in a rut, but blogging was something that just gave me renewed energy and re-lit a fire that was dwindling in my main medical career.


  2. I am probably a combo of escape artist, bored, and (almost) empty nester. My wife accuses me of being a premature empty nester, and she is probably correct.


  3. I think there’s a subset of the escape artist and that is the person who will HAVE to change jobs soon and is trying to prepare for that. Perhaps that category could be called The Parachutist? It’s a person who’s on their way out of their main job but can’t or doesn’t want to stop making money yet. I’m an example. I’m a full time ED doc but I recently found out I have a neurologic disorder. Now I can hear the timer ticking down on my clinical career. Gotta land safely, though, and I’m looking at graceful ways to transition out of clinical medicine and into something less physically taxing that I hopefully won’t hate. Great post!


    1. I’m sorry to hear about your diagnosis, but for your sake I’m glad you have time to pack your parachute and pick a drop zone. The beauty of emergency medicine is we are comfortable with a breadth of medical conditions that span inpatient and outpatient medicine. That leads to lots of alternative job options. Good luck!


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