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5 Steps to Getting Paid to Do What You Love. It Might Not Be as Hard as You Think.

How can you do what you love?

I watched an interview once with an entrepreneur. She loved what she did so much that she couldn’t wait to get up in the morning. She told the interviewer that she woke up at 5:30 am without an alarm clock and rushed to start her day, because she loved it that much.

Come on. Really?

Well, as I dragged my sorry ass out of bed every morning to haul into the city for a job that I hated, I figured that it was probably bullshit.

But then something happened. I started Roostervane.

I found myself sitting on my laptop at 5:00am writing posts. I couldn’t wait to get up and start, logging at least an hour before I jumped on the bus to work, where I’d write for another hour until I got downtown.

The old cliché clicked in, and I found myself following my passions, my dreams, and all that other stuff I thought was crap.

This isn’t my full-time thing yet, but I’ve already made some interesting discoveries about how to get paid to do what you love.

Here are five steps.

Step 1 – Be Honest About What You Love
Step 2 – Be Creative About Making Money
Step 3 – Constantly Develop Your Skill
Step 4 – Build Your Personal Brand
Step 5 – Jump When the Time Comes

1.      Be honest about what you love

You only sort of like the thing you’re getting a degree in. You tolerate it and have some natural ability.

So why the fuck would you expect to step out of a degree that trained you in something you only sort of love and find a job that you 100% love?

Okay, to be fair, there are times when we grow into a career. You might get on a team that inspires you, and they pick you up a bit. You might enjoy a project.

But the drive in your soul should come from doing something you actually love to do.

So let me tell you what happens for a lot of people. They do a degree that makes sense. The adults in their life encouraged them to do it. So they go train for this degree—because a degree is always a good investment, right?

Then, they get to the end of the degree and start looking for somewhere they can use it. They apply to job postings that fit and hope to God that they’ll “find their passion” in that job.

It’s bullshit. Most people aren’t wired this way.

I get messages 100 times a week from people who are waiting to fall in love with a path they never really chose in the first place.

You might be waiting a long time.

If you want to love what you do, do what you love.

Now, I’m going to talk about the money below. I’m not telling you to quit your job tomorrow and go start auditioning for Broadway.

But start here—be honest about what you actually love. The cliché question holds up here: If you won the lottery, what would you spend the rest of your life doing?

ADMIT it to yourself. Don’t be scared.

I did a PhD. I worked in research and policy. I did very serious analysis and worked on international files. I still do a bit.

Do you know what I love?

Writing blog posts.

I have been writing for well over a decade, and I have hard drives stuffed full of forgotten novels and screenplays.

I told myself, I love writing. In a perfect world I’d write full-time. But I can’t make a living off of this.

The voices that raised me rang in my ears:

Be practical.

Don’t quit your day job.

You need something to fall back on!

A degree is a good investment.

You have those voices too. I don’t know who they are or what they’re saying, but you’re probably listening to them.

When I talk to people about what they want to spend their life doing, the challenge is never getting them to dream; the challenge is getting them to say their dream out loud and admit it to themselves.

“I want to run for office.”

“I trained to be an engineer, but I actually love scrap-booking.”

“I’ve got an English degree, so being an editor is something I can do. But, to be honest, I’ve always wanted to teach guitar.”

“I really want to work for the UN running programs around the world, but that’s crazy, right?”

Whatever your thing is, you owe it to yourself to admit it. Say it out loud.

Now.. Say it.

I can’t hear you.

Stop asking other people what you should do and be honest with yourself about what you want to do.

2.      Be ruthlessly creative about making money

Sandra didn’t think much of it when she picked up an old dresser on the side of the road. It was beat up, but she thought it had a lot of character.

She brought it home, sanded it, and painted it. Then she put a picture on Facebook.

The messages started coming in.

“Is it for sale? I’ll give you $75.”

“This would look so good in my bedroom! I’ll give you $150 for it.”

She sold it, and a week later found another one. She created a Facebook page, and put up a picture of her second flipped dresser.

The rest is history. She makes well over $100k a year, and her husband quit his job to flip furniture with her.

If you want to follow your passion, there’s no reason you need to be poor forever. Passion and money do not have to be mutually exclusive.

But you have to pay your bills somehow, unless you have a trust fund.

In another post, I described it like this:

You need an income and a calling.

Some people work a job that’s okay for good money and spend their spare time making model railroads in their garage. Totally fine.

But if you want to do what you love, it’s quite convenient if you can get paid for it.

The question is, how?

Will a company pay you as an employee?

Will you need to start a business?

Can you be a consultant?

Can you sell a product?

There are a million ways to make money in this world, so don’t be limited to paycheck thinking alone. Try to figure out the way that you can make the most money for the thing you love.

3.      Constantly develop your skill

My friend is a pretty-good musician. He was just one of those people who could pick up an instrument and play it.

But he believed that to be a musician was to be a type of savant, that talent was a blessing that shouldn’t have to be developed.

So, he didn’t practice. He didn’t dedicate himself to growing his skill.

Today, he can play a mean campfire guitar. But he’s not going to make money off it anytime soon, despite his dream of being a professional musician.

The thing about getting paid to do what you love, is that it also has to fit a niche for something someone else needs or wants.

The best way to do this is to keep developing your craft. Work on it so that you’ll be the best, and when the time comes to get paid for it, you can charge appropriately.

Figure out what it takes to get better at the thing you love.

Skillshare is a great way to develop your passion. We love it and we never encourage readers to use something unless I use it myself.

I love Skillshare so much that I became an affiliate for them–I get a commission when you sign up through that link at no cost to you. This helps support the work Roostervane does.

4.      Get Noticed- AKA build your personal brand

So, you are doing the thing you love. You are the best copywriter, painter, engineer, epidemiologist, biologist, or dancer.

You need people to notice you.

If Sandra had just painted the dresser, she would have had a nice piece for her house. Because she took a picture and put it on Facebook, she has a business.

This is the basic lesson. If nobody ever sees you do it, they can’t pay you for it. If a lot of people see you do it, and do it well, they can pay you.

So, branding has become a requirement for most of us.

  • If you dream of becoming a program manager for a UN agency, become a thought leader on LinkedIn (while also developing program management experience).
  • If you want to be the leading psychotherapist in your city, have a website people can find that’s well-branded, easy to read (perhaps even with some actionable tips), and be the first one that comes up on Google when they search.
  • If you want to do communications for a big company, build your portfolio online with blogs and articles that people can read.
  • If you want to sell crafts, open an Etsy shop.
  • If you want to become the expert on turning degrees into careers, start a blog about it (*waves hi*).

5.      Be brave enough to jump when the time comes

The final thing I’ve noticed about people who get to do what they love is that they have the courage to take a leap of faith towards it.

No, don’t quit your job tomorrow. Develop an exit plan (I talked about it in this post). To quote Dave Ramsey: “Get the boat a little closer to the dock before you jump.”

But then do it. When you can see the path, go for it.

We all have that friend, don’t we? They’ve been talking about their dream for years.

“I’m going to open a craft brewery.”

“It’s been ten fucking years, Tony! Do it already!”

“Well, I gotta wait until all the ducks are in a row. Gotta get the house paid off. Gotta wait till the kids are done school.”

And then the classic:

“Good things come to those who wait.”


I’ll tell you what happens to those who wait. They get to watch people with less talent dominate the marketplace, because those people had the guts to jump.

“I’m a better singer than Britney Spears.”

Well she’s making millions and you aren’t.

I see people with a lot of education complain about this all the time.

“Why is Bill Maher being interviewed about religion? I have a PhD in it!”

Well guess what? Bill Maher built a brand and you published journal articles that 10 people have read.

I’m sorry to say that journalists looking for commentary on religion don’t read the top academic journals. They google.


People talk. Talk is easy.

Few people are brave enough to step up and do what they want to do. Build your courage so that, when the time comes, you have the ability to jump. Surround yourself with people who encourage you, rather than the losers who hold you back because your dreams threaten their comfortable mediocrity.

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