7 min read

These are the BEST and WORST things about self-employment, according to 5 creatives 👩‍💻

Being your own boss is a double-edged sword. I asked 5 full-time creators to break down the perks and downfalls of self-employment.
These are the BEST and WORST things about self-employment, according to 5 creatives 👩‍💻

We're entering a new era of work where self-employment is becoming just as commonplace as traditional employment. Thanks to the internet, anyone is able to build a business, audience or unique career path armed with nothing more than a laptop and some free time.

Update: This post inspired a follow up article which offers a direct-comparison between employment vs. self-employment, and the pros/cons of each. ⚖️

But is being your own boss all it's cracked up to be? For me, the transition from full-time employee to 100% self-employment was a rocky one. I had no idea what I was doing (and still don't most times) but after 3 years I can say it was the best decision I've ever made in my career.

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Entrepreneurship isn't for everyone - but for a new class of creators, it's the perfect mix of freedom, fulfillment and flexibility... with some caveats thrown in.

That's why I asked 5 full-time creators what the best and worst things about being their own boss was. I interviewed designers, video producers, retail business owners and online business owners. Here's what they said.

It's important to us to support creators, so when using this photo please give photo credit to Kati at xilophotography.com; Instagram @xilophotography. The creator featured can be found on Twitter @csallen. Full story: convertkit.com/courtland.
Photo by ConvertKit / Unsplash

✅ Best parts about being self-employed

🌎 Freedom & Flexibility

"One thing that I love about it is the freedom to make my own schedule (most of the time 😉). While this can of course be stressful at times, there's a sense of liberation in knowing that "ok, today I'm going to wake up and go for a swim at the beach before work" as opposed to stressing about the boss busting my balls for being late."
- Darbi Nicole, Complicated Co.

"Being fluid. If (let's be honest WHEN) life blows up, you don't need permission to process it. You make the call, cancel if you need to, but you can do right by yourself and your team. I love that so much."
- Megan Turner, Poppy Plum Media

"I think the biggest part of all is having the freedom to do what you want when you want with whoever you want and not having to put someone else’s schedule before yours. If your loved ones and friends have certain days off then you have the complete flexibility to spend time with them if you want to, your time and freedom is not controlled by someone else’s schedule."
- Miguel Bautista, Bautista Media

"The freedom actually comes in different forms. The most important benefit for me is being able to freely shape your impact in the community. My freedom comes in being able to give support back without limitations."
- Tony Kwon, DV - Yates Espresso Bar + KWON Media Studio

💜 Fulfillment

"One thing would definitely be the satisfaction of building/creating a business on my own (of course, I can't forget the people that I collaborate with on projects as well) and the sense of empowerment this gives me to know I don't need to be working for a big corporation in order to survive."
- Darbi Nicole, Complicated Co.

"You can over deliver! Sounds crazy, but I really enjoy giving clients what they don't expect. Great example: they're always blown away when we pick up the tab for lunch. Not a huge deal at all but I know as the owner that we can swing it, so I do."
- Megan Turner, Poppy Plum Media

💰 Earning Potential

"You literally have the ability to work as hard and make as much as you like, and you’re paid based on the value you bring to the market - not necessarily your time."
- Miguel Bautista, Bautista Media

🚀 Personal Growth

"The biggest hurdle is getting started and realizing that starting a business is never about the great idea or the next big thing - it's all about relationships.  Whether that is relationships with client who will be your first customer (the easier of the two ways) or relationships with technical partners (software engineers or marketers) to help you bring it to life to get clients."
- Michael Young, SharedConstructionContent.com

"It teaches you how to be independent and trust your gut and believe in yourself. With great power comes great responsibility, and with the freedom that is granted to you, you must learn how to focus your mind on your goals and hold yourself accountable as no one else will walk you to success when you were self-employed."
- Miguel Bautista, Bautista Media

Tony Kwon spinning up bass-heavy tracks and frothy lattes at DV - Yates Espresso Bar

❌ Downsides of being self-employed

🥸 Imposter Syndrome

"My biggest con of running my own business is my own internal fear. What I ask myself when I wake up every morning, and what I go to bed thinking every night, and what crossed my mind most hours is... "is it enough?"

I struggle with it everyday - am I, is it good enough? Will I produce an end-product/output that is good enough.  Will it meet the needs of my client or did I mess it up. Is my marketing good enough? Is my SEO good enough? Are my blog posts helpful enough? Do I treat my employees and contractors well enough?"
- Michael Young, SharedConstructionContent.com

👒 Wearing all-the-hats

"The biggest con is probably that you have to be all things sometimes. No one can be good at everything and sometimes as an entrepreneur you have to do things you know aren't your skillset simply because they need to get done. For me, that is usually organizing things lol."
- Megan Turner, Poppy Plum Media

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😵 Responsibility

"The biggest con would be the level of responsibility. It’s a double edge sword because while you do have unlimited potential to make money there’s also a bigger risk. You want to take a month long vacation? For sure go right ahead! No one is stopping you.

Just be prepared to deal with the other side to that which is working your butt off when you get back / running a team remotely while your on vacation / creating systems that make sure your business doesn’t die when you go away for 3-4 weeks."
- Miguel Bautista, Bautista Media

⚖️ Finding Balance

"The biggest con of being self-employed is that there really is a boss above you. It's your own ambition. One really needs to carefully work out the terms of your job, your goals and your benefits. But most importantly work out vacation pay, or else there are no days off. Make sure your ambition is balanced with the quality of life."
- Tony Kwon, DV - Yates Espresso Bar + KWON Media Studio

"While being self-employed essentially gives me the liberty to make my own schedule... the con to this is that often there is this looming assumption that this must mean you are "available 24/7". Setting boundaries with clients (and sticking to them) can be challenging, but hey, we're humans who need a personal life and down time too!"
-Darbi Nicole, Complicated Co.

“One of history’s few iron laws is that luxuries tend to become necessities and to spawn new obligations. Once people get used to a certain luxury, they take it for granted. Then they begin to count on it. Finally they reach a point where they can’t live without it.”

Yuval Noah Harari, renowned historian and author
From his 2014 book, “Sapiens: A Brief History of Humankind.”

What’s trapped you?
Photo by Victoria Heath / Unsplash

There are pros and cons to every career path. The thing I love most about these creators is how they've weighed all the factors in order to build businesses that serve their lifestyles. Each of them gets to do work they love for clients they adore.

Each path is vastly different. There's no correct way of doing things. The most important thing is being realistic about your current career and whether or not it serves your goals, ambitions and lifestyle. If not, the next step is being willing to do something about it.

There's a unique career path out there for everyone. You just have to find it.


🙏  I wanted to give a big thanks to Miguel Bautista, Megan Turner, Tony Kwon, Darbi Nicole and Michael Young for their help on bringing this together. Also wanted to thank my friends James King and Christian Charlesworth for being my second set of  eyes on this. Appreciate you all.

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