The Truth About Self-Employment

As some of you know and have been amazingly supportive about, I’m self-employed again. I was self-employed for 8 years before, then took a staff job for 2 years, and am now back at it. I’m in week one of my corporate-life retirement, self-employment-life-re-journey. There’s a lot to say and share, and I’m sure within 6-months I’ll look back at this and think how naive I was and how much more there is to say. Let’s face it, Lessons Never Stop.

So here’s the truth about self-employment from my own personal perspective (to date):

Whereas I was once exhausted every morning, even though I could sleep until 8:15 before getting up for my job, I now have endless energy. I can sleep with a generous dose of interruption and wake up excited to start the day. I’ve been going to bed past my usual bedtime and waking up around 7:30 without an alarm clock. I love being out and about all day.

Before I could barely muster the energy to make dinner. Life feels full of endless possibility again, whereas just a few weeks ago it felt decidedly beige. I’m writing from the divinely gorgeous NYC Public Library and noticing the raptured awe of the tourists popping in as a reprieve to the cold. I look at them and feel like one of them, knowing I can do anything I want tomorrow.

The sweet comfort of having a staff job, punching in, doing work that is tasked to you and enjoying free snacks and beverages from the communal kitchen is easy. So is having people there that will generally support you. And so is having free office supplies. Self-employment is typically days on end of solitude where you don’t know where work starts or ends. Having someone tell you what to do at work is simple. Can you motivate yourself to focus on your work, and create new opportunities for your self?

If you can’t self-motivate yourself to do much on your own in life, self-employment is not for you. In countless ways, I work harder at self-employment and take less than glamorous jobs to get by when needed than the hours I put in on staff. I have to find my own work, design my own projects, and stay motivated than watch the hours slip away having fun on Twitter or This week, I didn’t have any work lined up on the creative side. So I did some transcribing, which I strangely enjoy (you get to listen to people interview fascinating people and get into this groove where you’re productive yet zoning out and letting your fingers do the work. It’s all about reflection).

But yesterday’s project was akin to transcribing a riot. The recording was done in the food court of a mall and I ended up with a splitting headache. Yesterday, I got to take my friend for a coffee around the corner from my apartment to a place we call “the muffin situation”. It was sunny, gorgeous, and I knew I could control my own schedule. I can schedule acupuncture, going to the gym, bills, phone calls, or return emails whenever I damn well please.

There is no magic check going into your direct deposit every two weeks. You have to work for every dollar, and suddenly buying coffee is a direct correlation to how long you worked. People tell the self-employed that “you’re lucky” (or crazy) as if hard work has nothing to do with your life situation. Work is a choice. If you’re deeply unhappy at work, tell yourself you’re choosing to be there and come up with a life plan. If you’re not sold on that idea, just read this blog. Procrastination is often a form of rebellion and/or depression.

Try to motivate yourself out of that and see how difficult it can be. Now consider no one will put a magic paycheck in your account if you don’t hustle for the next gig. If you mess up at work, you usually get over it fairly quickly, or the rest of the team is somehow involved and absorbs some of the pressure. If you mess up your self-employment, you lose clients and money. The pressure is heavy, even for projects you’re doing just to get by.

The ability to work from an intensely gorgeous and exciting locale, like Vermont or Miami, is exhilarating. The reality of staying put and working on a project when a brand new world is waiting for you is excruciating. Not everyone is built for self-employment, nor wants to be self-employed. I am telling you now – that is okay. But consider this. I watched a video with Pamela Slim and she reminded us that everyone is self-employed, even if you’re at a staff job.

There is no real security and your life choices are up to you. So if you’re telling yourself you don’t want to give up the security of a job, that’s an illusion. Stop letting it own you. Stay healthy. Mind your weight. Dislike networking? If you think it’s too intense at work, consider doing it by yourself with no group of peers to cushion the awkwardness. You have to figure it out or be satisfied simply treading water for a living. Self-employment means creative problem-solving.

If you can’t think fast on your feet and come up with creative solutions, you’re probably in the wrong business. Understanding psychology is one of the most important things you will ever do for yourself in terms of self-employment or any business endeavor. What do your clients need? Really need on a deep level? Figure that out first because they certainly won’t give a crap about what you need. The idea that you’re not in control of your life and are tied down to something you don’t enjoy is a fallacy. So you might as well live life from the freedoms of self-employment if that’s where you know you’re called to be. In conclusion: Self-employment rocks. But like most incredible things in life worth living, it takes everything you’ve got to leap and land on your feet.