Self-Care For The Self-Employed

Neal Ungerleider
New Transmissions
Published in
6 min readOct 6, 2016

A Guide For The Self-Employed, Freelancers, And Independent Contractors

Self-employment and being your own boss are awesome. Self-employment and being your own boss are also difficult sometimes. Most worthwhile things in life are contradictions, and working for yourself is no exception. That means self-care, strategizing, and making sure you don’t burn out in the process.

Here’s the funny thing about freelancing, or consulting, or running your own business: From the outside, it looks amazing (and it is!). But on the inside, you’re dealing with a lot of variables. You miss the small talk and coffee schmoozing of a conventional workplace. You pay a lot of expenses out of pocket that your employer usually pays for. When you’re working on projects, you frequently work on your client’s schedule rather than yours — whether or not that schedule fits in with your existing work commitments.

Self-employment: You never thought you’d miss coworkers, but you do!

And, most importantly, you’re wearing more hats than you did when you worked for a conventional employer. Whether you’re a writer, a motorcycle mechanic, or a software developer, you’re responsible for finding new clients, chasing unpaid invoices, and taking care of taxes.

I know this from personal experience. For the past decade, I’ve worked some permutation of full-time, part-time, and freelance work (mainly as a journalist at places like Fast Company) at any given time. At the beginning of 2016, I made a big life change: I switched from full-time journalism work to relying on content consulting and ghostwriting for the bulk of my income.

Here’s the thing, especially for folks like me who come from journalism backgrounds: We talk to a lot of people. We accumulate tips along the way. I spoke with a lot of smart people about how they avoid burnout, maintain personal relationships, and take care of their mental and physical health while being self-employed. Here are five of the most important things I learned:

1. KEEP THINGS ORGANIZED: I can’t stress it enough — if you’re working for yourself, you need to keep things organized. Embrace your inner Felix Unger and keep track of everything.

In my work on the wooly fringes of marketing and content development, I use a whole bunch of different tools to keep track of my work. That means using Trello to keep track of projects and due dates, Todoist to create a to-do list of individual tasks, Evernote for storing information and notes, Hubspot’s free CRM to keep track of potential clients and potential projects, Xero to handle bookkeeping and accounting, Google Calendar to block out time every day, and a paper notebook at my desk for brainstorming and jotting ideas.

Your individual mileage will vary depending on your personal needs and preferences. It doesn’t matter whether you prefer paper notebooks (The Bullet Journal is awesome) or apps; just keep things organized or you’ll suffer the angry wrath of a million lost emails, project due dates, and forgotten tasks.

2. YOU NEED A WORKPLACE: Home is home. Work is work. You can work from home, but you can’t work in the same space where you sleep, eat, and relax.

Here’s the thing: People say they’re good at compartmentalizing, but that’s not the case in real life. When we work on the same sofa where we watch Netflix, we tend to want to watch Netflix. When we’re working at the same table where we eat dinner, we want to eat.

I’m a big fan of coworking spaces for jobs which are based around working on a computer. I live in a city that’s not New York or San Francisco, which means I’m lucky enough to have a separate room in my apartment for a home office (and keep a part-time coworking space membership as well).

If you can’t afford a coworking space, or are working from home while parenting/looking after family, try to work as often as possible from outside spaces such as libraries and coffeeshops. Which brings us to….

3. GET OUT OF THE HOUSE: Something funny happens in the workplace. You interact with a group of regular faces you see day after day, and share the joys and headaches of work with each other. Although coworkers can get annoying at times, they’re also people who are going through the same experiences as you. That’s something everyone needs.

The challenge for the self-employed is that they don’t have any coworkers. That means, in many cases, a lack of social interaction at work. No matter how introverted or extroverted someone is, that’s a bummer — and a quick way to become an unhappy hermit.

I make an effort to have lunch at least twice a week with fellow self-employed folks or work contacts who are in easy commuting distance. When I can’t do that, I work from a coffeeshop or something similar. Don’t underestimate the power of lunchtime gossip and idle industry talk — it makes a huge difference in mood.

4. WORK-LIFE SEPARATION IS AWESOME: Freelancers and the self-employed have a habit of blending work and their personal life. This is something that’s awful and counter-productive and has to stop.

Unlike most employees, who have a more-or-less clearly defined set of job responsibilities, and set work hours when they’re on the clock, self-employed people make their own schedules. This means that, hypothetically, you can take on as much work as you can handle.

But here’s the dark truth: If you take on too much work, the quality of your work suffers. Your clients notice the missed deadlines and poorly executed projects, and that’s just the work side of things.

Having work bleed into your personal life is a great way of alienating those around you, of ruining your relationships, and of priming yourself for nasty things like burnout and depression. You don’t want to do any of these things — pace yourself and make sure you’re spending time with people you care about, exercising, and doing fun things outside of work. If the President of the United States has time to play golf, you have time to play Fallout 4 for a few minutes.

5. SCHEDULE TIME OFF: Did I mention yet how freelancers and self-employed folks have to serve as their own sales reps and business development teams? And that they’re doing that on top of the work people actually hire them to do? That gets kind of exhausting sometimes.

No matter what the nature of your self-employed work, you want to make sure you’re resting before you’re tired… and that you’re taking time off to avoid on-the-job burnout or exhaustion.

Because you’re working on projects for clients, the odds are good you’ll have your share of hectic rush projects. Days upon days of 11 hour workdays aren’t good for anyone, and you’re deluding yourself if you think you can manage that workload as a single employee over an extended period of time.

Figure out when your slow stretches are going to be, and intentionally book mornings/afternoons and entire days off in advance. Work hard when you’re working on projects, and schedule relaxation time in between the crunch cycles.

Obviously this goes without saying, but this is just my own personal advice on self-care for the self-employed. If you have your own tips or think I’m completely off-track with my suggestions, I’d love to hear from you in the comments.

Working from coffeeshops costs money! Support Neal’s latte habits and send a few dollars via PayPal.

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Neal Ungerleider
New Transmissions

Writer who does consulting-y things. Journalism work seen: Fast Company, Los Angeles Times, Dow Jones, etc. Child of the Outer Boroughs.