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This article was published on May 2, 2015

17 life lessons from professional freelancers

17 life lessons from professional freelancers
Shannon Byrne
Story by

Shannon Byrne

Shannon is the Chief Content Officer for CloudPeeps , where she crafts words, creates strategies, and recruits loyal brand advocates. She's Shannon is the Chief Content Officer for CloudPeeps , where she crafts words, creates strategies, and recruits loyal brand advocates. She's also the founder of <a href=”“”, hand-curated songs delivered to your inbox, and an enthusiast of live music, sunshine, craft beer, and quality content. She’s in Brooklyn, NY. Say hi <a href=“”@ShannonB”

Shannon is the Chief Content Officer for CloudPeeps, where she crafts words, creates strategies, and recruits loyal brand advocates. She’s also the founder of, hand-curated songs delivered to your inbox, and an enthusiast of live music, sunshine, craft beer, and quality content. This post originally appeared on the Cloudpeeps blog.

Freelancing full-time can be a scary concept to think about. It’s a risk to leave your stable job with benefits to become responsible for your own time, invoices, deadlines and paychecks. We get it, just the sheer thought can be overwhelming.

Considering that 18 million people in the U.S. alone (according to MBO Partners) have taken the leap — so many of which are successful — and bearing our own experience in mind, we’re confident in saying it’s not so scary once you’re in it. Rather than expecting you to take our word for it, we spoke with a few of our favorite successful freelancers to share their stories, tips, and what to expect when going to work for yourself with you.

Want to know what it’s like to freelance, but not ready for the full-time commitment? Dip your toes in the freelance pool, sign up to be a CloudPeep and check out the part-time gigs available on the platform. In the meantime, check out what the pros have to say about it.

Paul Jarvis, Designer + Writer,

Paul JarvisPaul is a designer, writer, and teacher of things. His Sunday Dispatches are one of the few email newsletters I read religiously, and his books are super insightful too. He also teaches online courses and co-hosts a podcast, all of which you can find at

Paul has been freelancing almost his entire career (17 years of it), making quite the name for himself, but not without learning a few lessons along the way.

Falling into freelance

Q: At what point did you realize that you needed to work for yourself rather than get a “traditional” job?

A: To be honest, I stumbled into it. I worked for an agency in the 90’s for about a year. Their vision and values didn’t align with my own, and more importantly, how they treated their clients wasn’t up to par with how I wanted to treat clients…so I quit.

I was going to go look for another job the next day. But then, I kept getting calls from the clients of the agency telling me that they knew I did all the work, and they wanted to bring their business to where I was going next. After the third or fourth call, a lightbulb went off in my head. I figured, why bring all these clients somewhere new, why not just work for them myself?

So that’s what I did. I started my company (all the government paperwork) the following day and got to work the day after that. That was over 17 years ago now.

Taking control

Q: What did this decision making process look like?

A: My options were essentially this: Go work for someone else who may or may not align with how I viewed my work and communication with clients OR create my own business where I was in charge of the work I did (or didn’t do) and how I communicated with clients. So for me, it was easy — I wanted the control.

Crafting your lifestyle

Q: What improvements have you seen in your lifestyle since choosing to work for yourself?

A: At first, working for yourself tends not to be an improvement. You have longer hours, more work, no benefits, less stability, etc. But then, hopefully, over time, you can start to craft a lifestyle for yourself that lines up with how you want to work.

For me, I value freedom more than money. I work hard when I have to work, and then I don’t work at all for at least a few months per year so I can focus on other things. That’s changed a lot from when I started since I wanted to make ALL THE MONIES back then.

Finding your tribe

Q: Any surprising advantages or disadvantages to working for yourself? To working remotely?

A: All of my clients are remote, so it doesn’t matter where I live. That’s why I live on some property in the woods, far from the nearest city or town. The advantage (for me) is being able to pick where I can call home.

The disadvantage I’d say is that working for yourself can get lonely. I actively try to schedule some “hangout” time on a weekly basis with other freelancers and am pretty active in some Slack channels that are more like water coolers than specific work-related chats.

Setting up a mental space

Q: Any specific tips for people considering freelance and remote work?

A: The biggest thing about remote work is being able to work with distractions that you can’t avoid and setting up a mental space for yourself that removes as many distractions that you can avoid.

For me, I have a room in my house that’s “an office.” So if I’m in there, I’m at work. There are no personal distractions in there. And, when I’m done for the day, I leave that room. No one bugs me when I’m in my office working unless it’s a critical issue, and conversely, I don’t answer work-related emails/calls when I’m not in my office. The separation helps with sanity (apparently).

Carly Ayres, Content Strategist,

Carly AyresI first met Carly at an event where we both were awkwardly forcing ourselves to “network” and immediately clicked. Maybe because she’s also from Florida, or perhaps because she’s unapologetically herself, which I respect. At the time, she was leading content full-time for CreativeMornings. About seven months ago, she made the leap into freelance and has secured some really cool projects while enjoying the freedom to continue doing what she loves.

Finding work that you love

Q: What are you currently working on as a freelancer?

A: At the moment, I am super excited to be working with The Great Discontent on #The100DayProject, helping highlight and curate all the amazing content in weekly newsletters. It’s been exciting and overwhelming all at once to see all the fantastic projects people are working on, and I am looking forward to watching them develop over the weeks.


I also work on another newsletter called unti-tled (, as well as heading up social media and content strategy for Collaborative Fund and a few other clients. Needless to say, I keep busy.

Making the big decision

Q: What made you leave your day job to pursue a freelance career — what did that decision making process look like?

A: Leaving CreativeMornings was one of the hardest decisions I’ve had to make. Being my first job out of college, CreativeMornings provided a great opportunity to really dig in and help develop the content strategy for a company in its early stages. I joined right when we launched the Kickstarter campaign for the new site and watched the community grow to more than 100 chapters around the world.

I will always be grateful for the incredible amount of trust and freedom I was given there, as well as the ability to be a part of the amazing community full of kind, talented folks at Studiomates. Being surrounded by so many people more experienced than myself who were always happy to offer advice and support when needed has shaped everything I’ve done since.

That being said, after a few years at CreativeMornings, I found myself with the familiar itch to try something new. I had been steadily taking on more freelance work and realized that the work that truly scared me — the work that was really pushing me past my comfort zone and challenging me — was the projects I was taking on after hours and on weekends. I realized that if I was to continue growing, that was the work I needed to be doing.

That realization made things a little bit easier, along with the fact that I now have hundreds of CreativeMornings friends around the globe willing to give me a couch to crash on.

Hitting your stride

Q: What improvements have you seen in your lifestyle since choosing to work for yourself?

A: Seven months later, I can wholeheartedly say that the change has been amazingly positive. If you would have asked me five or six months ago, maybe not so much.

It took me a few months to hit my stride, determining how much work I could realistically take on, figuring out how much to charge for said work, as well as developing processes and systems for tracking projects and managing workflow.

On the other side of that, I will inevitably have to jump many more hurdles and am still learning a ton, but if I wasn’t, I suppose I wouldn’t be doing this.

I can happily say that I now have a gym membership and occasionally cook myself dinner, which I feel like is a sign of somewhat successful work/life balance.

Finding a community

Q: Any surprising advantages or disadvantages to working for yourself?

A: I think the ability to control my own time, set my own goals, and pursue the projects that are interesting and challenging to me are all the clear benefits of working for yourself — they’re also the disadvantages.

That’s why it’s so absolutely vital that you have a community as a freelancer. Find the people who will give you advice, feedback, and help you bounce around ideas. Just as no (wo)man is an island, neither is a freelancer and I find that I need to constantly seek out other opinions and ideas.

Identifying the real cause of issues

Q: Any tips for other people considering freelance and remote work?


  • Find a community.
  • It’s never about the thing.
  • Always assume the best, unless proven otherwise.
  • Every issue is a communications issue.
  • Always keep growing.
  • Do some form of exercise every day.

Julie Chabin, Designer, & Kimd

julie chabinJulie and I worked together at Mention. She’s an extremely talented designer and a blast to work with. When she left Mention, she wasn’t exactly sure what she wanted to do next and definitely did not want to settle. So she started to take side gigs and pursue freelance design full-time, booking herself solid six-months in advance, often working for the same client on different projects.

Making the most of flexibility

Q: You have your own project (Kimd). How has freelancing helped (or hindered) your ability to pursue entrepreneurship?

A: To be totally honest, I have been fully booked for the past few months and while this is really great, it also means I didn’t have that much time to work on my personal projects. Yet, thanks to planning flexibility I was able to be more reactive (mostly to fix bugs) on my projects than while I was working full-time for a company. If you’re trying to start your own company, maybe working part-time would be a nicer idea.

Becoming healthier

Q: What improvements have you seen in your lifestyle since choosing to work for yourself?

A: I’ve been eating much healthier. I used to eat fast food, pastas or chinese when was going out for lunch with coworkers or friends. Now, I can take the time to cook and eat real and delicious food.

Another thing changed: Because my home is also my workplace, it has to be clean everyday. I can’t concentrate if things are messy. Other than that, I work exactly like before, same software, same computer and settings.

Communicating more clearly

Q: Any surprising advantages or disadvantages to working for yourself? To working remotely?

A: Apart from the benefits of eating healthy, I lose less time in meetings. I also became more confident about my work and communication skills. Working remotely for someone forces you to express yourself more clearly. Plus, the distance gives me a perspective I didn’t have while working within a company.

Making sure you’re ready

Q: Any tips you have for anyone considering freelance and remote work?

A: Before pursuing a full-time freelance career, be sure you can afford to quit your job. Don’t start if you don’t have any contacts or contracts in sight.

Consider joining a community to share what you’re working on and collect feedback. I’m connected to others on several Slack channels everyday, and it gives me the feeling of belonging to something.

You’ll also need a lot of discipline to wake up in the morning and not push things back to another time. If you’re working from home, you’ll need to have a reason to go outside everyday and meet people. (Cats aren’t real people and their feedback sucks, don’t listen to them.)

Kate Kendall, CEO, CloudPeeps

kate kendallNow CEO of CloudPeeps, Kate has previously traveled the world relying on freelance social media and community management work for various companies, while also running her other company, The Fetch.

In the process, she realized that there was a surplus of freelance talent available in the market while companies were struggling to manage their social media and web presence on their own. Agencies are expensive and hiring is time and resource consuming. That’s what drove her to star CloudPeeps, which is now 1.5 years old with four full-time employees and a few contractors distributed in San Francisco, Lake Forest, New York, Seattle, and Berlin.

Focusing on freedom

Q: Why did you choose to make the CloudPeeps team remote?

A: It was a natural progression, not necessarily a decision made from onset. I’ve always been a huge fan of Joel Gascoigne and the team at Buffer, and have watched them successfully scale a team remotely in a fun format.

I love that remote work focuses on productivity, accountability, transparency, and trust while catering to different styles of work. I’m on the introverted side and find I get way more done working in a quiet, focused and peaceful space – most of today’s open cubicle settings are the opposite of this.

With the nature of our marketplace, it makes sense for us to practice what we preach. The bottom line is, that it’s about having the freedom to choose what works best for you.

Resetting your gratitude

Q: Any surprising advantages or disadvantages to working for yourself? To working remotely?

A: When you get accustomed to working remotely, self management and unlimited freedom – you can start to take it for granted. Every once in a while, when I’m getting cabin fever from working from home, or feeling less motivated, I go and do something I dislike doing.

This could be commuting during peak hour to go work out of an office, or spending a full day in back-to-back meetings or calls. This resets my gratitude index and I feel super thankful this is no longer the norm for me.

One of the criticisms of remote work is that it doesn’t facilitate the spontaneous social interaction that offices do. We’re in an age of abundant social contact – where you can connect with anyone, every hour of the day online or head to a plethora of events in any niche or professional network your heart desires.

I don’t seek more social interaction, I seek less of it and more of it with the friends and family that are meaningful to me. As much as we all love our colleagues, remote work allows us to spend more time on those people most important to us. You see a lot of remote work showcased in the form of digital nomads and travel, but the ability to positively impact families and moms is huge.

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Image credit: Unsplash