How to Thrive in the Gig Economy


The traditional thinking about careers and business is that when you have settled on a course, you have to ride that road down to the very end.


The thing about a road is that you can just step off it!

People think about their lives as if it is this preplanned highway when it might as well be the Oregon Trail. Its a suggestion not mandatory for you to go to college, find a traditional 9-5, or I guess in this metaphor, Oregon.

Why not just take a left turn at Albuquerque and see what happens?

We are trained to think that first, you go to primary school then high school then either university/trade school then get married have kids and retired then I guess, die?

This makes sense because for a brief shining moment from the 1950s-1990s that was a sustainable path. There were pensions and security when you followed that path.

For all my millennials out there, sorry boo, but that highway to prosperity has fallen into disrepair and you’re more likely to break down on the side of the road than find a pension at the end.

That means that we have to be clever and resourceful and willing to take ownership of our careers and businesses. There is no lifeguard on duty, babe.

Depending on your location, this might be more or less true, but even if you have strong unions, workers rights, and a stronghold against worse excesses of Late-Stage Capitalism, the gig economy is still coming for you. What you can do about this on the macro level is beyond the scope of this blog, but let’s dive into what you can do for yourself on the micro level.

Now, keep in mind whom I am writing this for- reasonably educated privileged people in the Western world. These tips can be useful for all, but they aren’t universal.

What can you do to thrive, not just survive, in this brave new world?


Job titles are becoming meaningless. We aren’t in a world where you have the choices to be a cooper, a baker, or a candlestick maker. Its all about skills and being able to adapt them to the jobs available. Not only do you need to focus on those skills, but you need to be able to identify how they are useful and THEN MARKET THEM.

It really chaps my hide when I see people who are like ugh, I have this 4-year degree and it’s useless then I find out that it is psychology. Really? You can’t see a marketable use for insight into human behavior in a time when so many jobs in tech, finance, marketing, social work, etc are all about understanding human behavior? Let me hit you with a clue, honey.

If I can make a history degree marketable… You can market communications, psychology, English, etc.


In the most educated generation in the world, you need to show that you can do more than sit in a chair and regurgitate information in the short term. Build a portfolio to showcase that you can actually put these skills into use. If you are a marketer, write a case study. If you are a teacher, show off a lesson plan. If you are a hairdresser, have some pictures of some cool hairstyles.

Come with the understanding that no company is going to train, mentor, or hold your hand on the job and you will never be disappointed.


The sad fact of being employed by most companies is that you are seen as expendable.

It doesn’t matter if your manager loves you.

It doesn’t matter if you made the company a million dollars last year.

It doesn’t matter if you have institutional knowledge that no one else knows.

They will shitcan you and have you train a younger and cheaper replacement.

Even in a startup where there are certain employees who are tentpoles for the whole operation, the founder is usually not smart enough to recognize that.

That means that you always have to think like a mercenary and be ready to move. Keep that resume and LinkedIn updated, keep your face familiar in the industry by networking, and never let that portfolio look stale.

Don’t be that guy fired on a Friday and packing up his desk with a shuttered look of shock.

Be the guy who can get fired on a Friday morning and by the afternoon already has an interview scheduled on Monday with his former company’s competition.


Understand that your value doesn’t come from your work. It doesn’t come from your production. It comes from within.

This can be a scary time to build a career, but let’s reframe that- its an exciting time to build a career.

This road might have its ups and downs, but you can be the one to pioneer a path that is uniquely you. It doesn’t matter if you live to work or work to live. You can design a career that brings you satisfaction and supports a lifestyle that you want whether you want to be a digital nomad in Bali or a domestic goddess in the ‘burbs.

Take ownership of your direction and you never know where the road might take you!

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