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Freelance Interview Series – Self Motivation with Michael Keenan

Michael Keenan is a freelance content writer and SEO strategist and the co-founder of Peak Freelance, a community that helps freelance writers scale their businesses. With over six years of experience as a writer and marketing consultant, Michael knows what it takes to grow a thriving freelance business. We talked to him about his professional journey, his growth goals, and how he structures his days to be successful.

Self Motivation w/ Michael Keenan

1. What was your motivation to start freelancing?

I’m rebellious by nature. Ever since I started working in restaurants at 12, I never got along with my bosses and would often fight with them. In good spirit of course: I questioned why they did things the way they did, fought for equality amongst employees, asked for more money religiously. You know, all things most managers hate, especially in restaurants. I was a young punk trying to shake things up a bit.

My mom taught my brother and me the value of independence at a young age, which aided my rebellious self. I hated school, authority, and anyone that tried to keep me in a box.

I worked, saved, went to college—did the things I was supposed to do. Then I moved to LA, lived out of a backpack, and traveled outside the U.S. I still, however, always ended up working in restaurants and bars when I was settled. I had the chance to work a few office jobs, but I could not bring myself to settle into the 9 to 5. It would crush my spirit.

It was in 2016 when I lived in Portland that I started hanging out with a different group of people: designers, writers, creators (before they were the hot thing), business owners. I had a friend who worked whenever he wanted and made a good living doing it. I came to find out he was a freelance designer, working on projects like The Sims and other enterprise games.

He encouraged me to go freelance, claiming it was my only way to get out of restaurants without working an office job. So I picked up my first gig writing about yoga and meditation off UpWork for $25. It was a tough first few years trying to build a writing business. I had no help or community.

My motivation was fearless independence. I wanted to build a cool life for myself. A life I could be proud of and make good money living. A life that would allow me to do whatever and live wherever, and earn money for myself rather than some C-Suite.


2. Do you set business and personal goals for yourself? If so, do you mind sharing?

Always. My focus for the past three years has been relentless business-building. I’ve been pouring all my time, money, and resources into building a freelance business, as well as Peak Freelance, and various investments in art, crypto, real estate, and restaurants. My personal goals align much with my business goals. However, I put them aside until 2022. More on that later.

My business goals have always been income-based. For example, my income goal for 2021 was $250,000 and I pursued that aggressively. I ended up making $307,000 freelance writing in 2021. Hitting that income goal moved me to the next stage of my business for 2022, building systems to replicate my writing style and quality to scale production. You could say my business goals have moved away from income only and toward scaling. My goal for 2022 is to up production without sacrificing quality.

Personal goals are a must for me. Again, I’ve been focusing on investing these past few years. I want to retire at 40, so keep that in mind. I am pursuing that aggressively. I had a lot of fun in 2021 with my business, but I realized there were some things I was missing in my personal life for the sake of income. So this year, my personal goals are:

  • Take my pups hiking once a week during a “work morning”
  • Cook more dinners for my partner and me
  • Learn how to make vapor twitch / downtempo music
  • Ditch my phone past 8 PM
  • Spend more time alone
  • Call my grandma more often

Simple things, but meaningful after going heads down into work for a few years.

My personal goals for the year are to take a step back and take more time for myself to explore other things. I have many curiosities and creative pursuits to be met, so I’d like to see them through in 2022.


3. How do you structure your day as a freelancer?

I am a 5AMer. Mostly because I like to be awake when the world is sleeping. I feel more productive than in the afternoon or at night. My days start around 5 and I start hitting the task list I prepared the night before. I usually work for two hours or so then go for a run or exercise around 7. When I come back I check emails and slack for 15-20 minutes, then play with my dogs, do house chores, shower, and have breakfast until 9:30ish. After getting some fuel and refilling my coffee, it’s back to the computer until about 2 PM. I can do a number of things around this time: meetings, writing, editing, planning, interviewing, tasks. Whatever my list tells me to do.

We eat lunch later here in México. So at 2 PM, I break for lunch until 3:30 – 4. Then I work from 4 to 6, which is usually the most boring and tedious tasks. Because I don’t like using my brain in the afternoon, no writing takes place during these hours unless I’m desperate and trying to hit a deadline (which fortunately doesn’t happen much anymore).

Then I’m free. The rest of the night is spent walking the dogs, reading, watching Netflix, or going out to an event or friend’s house.


4. What do you do when you’re feeling uninspired or unmotivated?

I reconnect with nature. That’s really the only thing that works for me. I get so bored sitting at the computer all day, every day. So when I am not motivated, I head for the outdoors. It can be a long hike, a weekend trip, or even taking the dogs to the park. Depends on my mood.

Sometimes I just like to sit outside, listen to the birds sing, and feel the wind on my face. A little bit of sunshine can do great things when I’m uninspired or unmotivated. Maybe I’m a plant.

Another way I get inspired is by going to an art gallery or museum. It’s like a brain massage and can get the juices flowing again after looking at words for too long.


5. Do you find email and social media to be inspiring or distracting as a freelancer?

I keep my phone on Do Not Disturb all day and shut off email notifications. I find email so distracting. I really hate it. So I check it maybe twice a day. I 1,000% prefer to answer a Slack or WhatsApp message quickly. All my important decisions are made there.

I keep all Twitter and LinkedIn notifications off on my phone also, not because I hate it—just because I’ve found it works better for me. I don’t have Instagram, Facebook, TikTok, or Snapchat. So I don’t have to deal with those notifications either.


Keep up with Michael on Twitter or check out Peak Freelance to dive into their expert interview series, job board, and more – all aimed at helping you become a more successful freelancer.

About the Author
Samantha is co-founder of Harlow. Previously she was a marketing and demand gen freelancer. She enjoys traveling, connecting with new people, spending time with her dog Karl, and throwing back an extra dirty martini every now and then.

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