5 Lessons from 5 Years of Freelancing

Every month, I pay my bills with dollars earned through my computer keyboard. Five years after leaping into the unknown — quitting my full-time job to move to Colorado — an experiment in freelancing has turned into a modestly successful writing and editing business.

Over the last few years, I’ve written marketing content for a variety of organizations: edtech, nonprofits, grant-making foundations, higher ed institutions, health tech, fitness, sustainability startups. I’ve reported on local policies and infrastructure (something I never imagined I’d be so fascinated by). I’ve introduced myself to complete strangers and seen those relationships lead to interesting projects. There’s work I’ve loved, work I’ve hated, and a lot in between.

Somewhere along the way, freelancing got not easy, but easier.

Clients returned for more of my services. Or recommended me to colleagues. Or tried to hire me full-time (no, but thanks for the compliment). And from my little basement apartment, I’ve kept writing and editing away.

To celebrate my five-year anniversary of freelancing, I decided to share five of the many lessons I’ve learned so far.

If you’re a fellow freelancer or thinking about diving in, I hope you find these lessons helpful. Freelancing is not easy and it’s not for everyone, but it can be done. It just requires self-discipline, some long-term thinking, and patience as you do your part. (A little luck can’t hurt either.)

Lesson 1: Work comes through relationships.

This year, most of my work has come through clients from previous years:

  • An agency I did random editing for recommended me to a startup that didn’t have the budget to work with them.
  • A nonprofit I edited for a few times over a year ago recommended me to another nonprofit for writing work.
  • An editor I worked with at a local publication approached me for an assignment at her new job.
  • An edtech company specifically asked to work with me because a company I worked with last year recommended me.

I’d heard from other freelancers that most of their work came through referrals, but this might be the first year that’s true for me. In the meantime, I’m still seeking to work with entirely brand-new-to-me clients because I like to do different things, work in different industries, and meet new people.

So if you’re just starting out or you’re a few years into freelancing and struggling to get work: Pour into existing relationships and introduce yourself to strangers.

If asking a total stranger out to coffee sounds awkward, think of it as meeting someone who’s interested in the same things as you: good content, engrossing storytelling, creative copy. You’re there to talk shop … and raise your hand for any freelance opportunities they might have.

For your existing client relationships, show up with your best and tell them about the other services you offer or types of projects you’re interested in. Don’t overthink this. A quick “by the way” in your next email can do the job. You may not get another project from them right away, but if they’re happy with your work and enjoy working with you, chances are they’ll want to work with you again.

Lesson 2: Run your business based on your goals.

It seems like freelancing internet is obsessed with making six figures. I, personally, am not interested.

I mean, if someone wants to hand me $100k (in a legitimate, totally not illegal way), I would accept it. But money for me is a tool that enables me to pay the bills and live my life. At a certain point, I’d skip the money so I can spend more time reading or writing for myself or embroidering or gardening or hiking or … literally anything other than working.

My goals for freelancing are not to make a fortune, but to maintain my freedom. I like owning my time. I like having the independence to turn down projects that I have ethical or moral problems with — or that are just plain boring. I like having time to pursue my own ideas, research what I’m interested in, and (slowwwwwly) work on my book proposal and eventual book.

I know how much I need to cover my expenses, put money away for retirement, save, give, and have some fun cushion. As a single, healthy, non-spendy, almost 30-something woman with no dependents, that number is fairly low.

What about you, fellow freelancer? What are your personal goals or reasons for freelancing? Money is a reality but it’s not everything. Is there something you want to accomplish creatively or professionally that the freedom of freelancing can help you achieve? Don’t get caught up in six figures talk if that’s not your goal.

Lesson 3: Put your personal projects first.

I’ve found whenever I’m getting annoyed or frustrated or bored with freelancing, working on my own projects is a fail-proof cure. Sure, my client work may still get on my nerves (this isn’t always the case, I promise!), but at least I’m feeling fulfilled in another area.

My first year freelancing, I started a blog about CrossFit in the Denver metro. The project, Denver Box Life, kept me interviewing and writing stories when I wasn’t landing any pitches and was making subsistence-level freelance income. I did a story each month, ran an Instagram and Facebook page for the blog, and drove all around Denver doing interviews. It was fun, introduced me to the area, and gave me more story samples when I pitched publications.

This year, I’ve been starting my work days with research for my book idea. I have a shelf in the living room where my research stack lives. Every morning, I sit in my purple suede bucket chair, grab the book I’m currently reading, and spend anywhere from 20 minutes to an hour absorbing as much information as possible (plus, taking notes and marking pages with endless stickies). It’s my favorite part of the day. Before I even glance at my email, I’ve accomplished something.

How do you do this if you’re not breaking even with your freelance income?

The answer depends on your responsibilities and needs. And whether or not you have savings to fall back on.

Be responsible about this. If you don’t have savings or if you have a family to provide for, you have to close that dollar-sized gap ASAP. Maybe you do this through freelancing, maybe you pick up a catering job like I did my first winter. Do what you have to do, but as soon as you can, prioritize your personal projects.

Why? Because freelancing, especially in the beginning, can be demoralizing — and working on your own thing can provide a sense of achievement or forward momentum when you’re not landing pitches or PLACE FREELANCE DREAM HERE. If you’re going to maintain creative sanity, you need to prioritize your own projects.

This also means you need to have your own projects.

If your freelancing goal is entirely dependent on other people commissioning you for projects, commission yourself for a project. I’m serious. The idea is to keep the object (that is, your creativity) in motion so that:

a) you maintain your creative sanity and

b) when you do land that pitch or FREELANCE DREAM OF CHOICE, you’re not so rusty and out of practice that the dream becomes a nightmare. =)

Lesson 4: Limit social media access during your working hours.

This one is really obvious, but: use a tool like BlockSite to keep you off social media during your primary working hours.

At the beginning of this year, I established a new rule that, with the exception of LinkedIn, I wasn’t allowed on any social media until after 4 p.m. on workdays. It’s wild how much more productive — not to mention, focused — I’ve been this year because of that one simple rule.

I used to get most of my work done between 2 and 6 p.m. because I spent so much time scrolling or checking notifications in the morning and midday. Now, when I follow the rule (which I do most days), I finish most of my work before 4, take a break to look at all the platforms, and then finish up the last bit of work. I’m less distracted and I waste less time re-training my attention on the task at hand.

Lesson 5: Be generous with breaks, especially if you’re stuck on a project.

Lunch breaks. Walking breaks. Nap breaks. Mid-afternoon dance breaks. All of these — and more — are absolutely acceptable. And they’ll support your productivity.

I’m a case study for all of the above. Most days, I take a lunch break of at least 30 minutes, usually longer. I listen to a podcast while making and eating my lunch, and when I’m done eating, continue listening. Sometimes I pick up a craft project or a deck of cards to keep my hands busy. Sometimes I just listen. Then I return to my desk.

Walking breaks I haven’t done in a while, but became the norm mid-pandemic and I’ll likely reinstitute them as the days grow shorter again so, you know, I don’t forget the sun.

Naps are pretty self-explanatory. Don’t overdo it with these, but if your body is tired, give it rest.

Mid-afternoon dance breaks — or their less time-consuming cousin, pushup breaks — are a way for me to release some excess energy when I really need to get things done but am too antsy to focus. They are also a great way to celebrate new assignments or getting edits back that are more complimentary than scathing.

That’s five lessons.

I’ll be honest: There are still days (weeks, months) when I wonder why I’m doing what I’m doing. Freelancing is hard. I miss the collaborative environment of the office. I miss coworker relationships and marketing department hijinks.

But with my limited time and energy, I can see freelancing helping me toward my long-term goals. And these lessons have helped me gradually build a still-evolving business that can support me as I pursue those achievable dreams.

Do you have freelancing lessons to share? I’d love to hear them!

Published by meredithsell

Freelance writer and editor. Nerding out over health & fitness, women's history, and untold stories.

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