Michelle Obama’s Career Advice Is Actually Amazing — But Only If You Let It Change Your Perspective

The way we think about work is completely outdated

Alan Trapulionis
5 min readMay 30, 2022


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Seven years ago, at 19, I got my first part-time job waiting tables.

I lasted a month before I got fired. It was the only time in my life I’ve had a job.

Since then, I’ve been side-hustling my way through life like there’s no tomorrow. Copywriting gigs, ghostwriting gigs, SEO stuff, self-publishing, reporting, blogging — you name it. If it has to do with freelance writing, I’ve probably done it.

I’m not proud of my career choices nor am I ashamed of them. Freelancing has been the norm for me since the beginning, and I don’t have anything to compare it to.

I do, however, notice a disturbing trend in how my philosophy towards work shaped up to be vastly different from peers who had chosen a more traditional path.

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The traditional way is to put all jobs into archaic categories and then expect them to make sense. I’m talking about labels like “writer,” “manager,” “director,” “salesman,” “businessman,” “journalist,” “programmer,” “consultant,” etc.

None of these categories have clear definitions anymore. Every writer must also be a businessman. Every businessman will inevitably have to play the role of a salesman. An actual salesman will probably make the most money consulting people, and so on.

I’m not even talking about the fact that any of these titles could define a myriad of different lifestyles.

For example, I know from experience that writing for Medium is an entirely different profession from ghostwriting for clients. It requires a completely different skillset, and it offers an entirely unique job dynamic.

I still feel uneasy when someone calls me a writer. J.K. Rowling is a writer. I’m just a guy who writes.

Some age-old professions hold true to their titles even today. A dentist is still pretty much a dentist, even if he owns his own practice. A lawyer…



Alan Trapulionis

In quest of understanding how humans work.