Self-Employment: Three Things I Wish Someone Had Told Me

The other day I received this text from a dear friend who had recently started her own business: “When you started your own thing, did you spend any time hiding under the covers?” Only the first three years, I replied.

There are particular inner difficulties in working for yourself. No matter how carefully your plan has been researched, how market-ready your idea is, how deep your faith, and even how much money you have, certain issues seem to arise. I began working for myself close to a decade ago and I’ve experienced them over and over. During this time, about 2 gazillion other people I know have started working for themselves and I’ve seen it in them too.

I applaud you, brothers and sisters! Please live your dreams. Please untether yourselves from the status quo. Know that you are extremely brave. And try to remember these three things.

1. Allow your daily schedule to arise over time and then have faith in it. When I first started working for myself, I tried to implement a schedule that mimicked as closely as possible the work I had just left (working for The Man in the entertainment industry). I sat down at my desk dining room table at 8a. I planned to “work” (on what??) as if I had a predetermined set of responsibilities. I broke for lunch at around 1. I planned to knock off around 6p.

I did it this way because I couldn’t imagine doing it any other way. Month after month, I forced myself to stick with this schedule because I thought that if I did not, I’d end up watching TV all day. Without a firm structure, I feared, I would not get anything done so I tried to replace the discipline of accountability to The Man with the discipline of…beating myself up.

It takes awhile to remove the harness of indentured servitude, so please be patient with yourself. Working on your own after years (or decades) of working for someone else often leaves an imprint of fear, lack of imagination, and self-judgment. Even if you revered your boss/company/mission, someone else has set the context and that “someone else” provided you with the safety and constraints of an other-referenced work setting. Thinking you can simply transfer that work ethic to your new situation is not only nutty, it is not good enough or big enough to serve your brilliance.

I tried to shoehorn myself into my old schedule for about 18 months when it dawned on me that I could do it another way. Instead of forcing myself to do this or that, I wondered, what would I do if left to my own devices? Would I watch TV all day? Would I sit at my desk, twirling a lock of hair and gazing into space? Would all my plans and dreams disappear into slothfulness?

Yes. On some days. But those days don’t trouble me as much as they used to.

This experiment was scary at first because I took away the net of predictability to find my own natural structure. I dropped what I was used to and also stopped listening to “experts” and their theories about productivity to see what my intuition told me to do. For some months, I experimented and it was from this that I learned to trust in my own crazy, circular, bumpy, odd process.

Here are the very loose parameters of the schedule that arose when I let my day unfold rather than hog-tie it to something external:

Do creative work in the morning, as early as possible. Try not to schedule anything, anything before noon. Safeguard this time. Even if I sit there twiddling my thumbs, sit there. Exercise before lunch. After lunch, do what takes the least amount of brain power. Towards the later afternoon, try to do some project planning. If I feel like working after dinner, I do. Sometimes I work on the weekends, sometimes I don’t.

This is what works for me, not you. You have to discover your own rhythms and this discovery comes only when you relax and allow your creative wisdom to guide you. It takes time. Throw in some good old-fashioned pragmatism and a couple of hard core reality checks and you’ll do fine.

Expect this to go fairly well about 30%-50% of the time. I know, that’s not a great percentage. But that’s how it is. Travel, loved ones, fatigue, and loss of heart can all interfere. That’s okay. It’s just you and you can figure out how to adapt.

This may always be a bit of a struggle but not because you lack discipline—because each day possesses so much possibility and so much richness that it is hard to figure out where to start.

2. Watch out for the roller coaster. The emotional ups and downs of working for yourself are extraordinary and have the power to dictate how you feel about your entire life. Someone sends you a positive email and you think, “This is working. I’m good at what I do!” Three people cancel their subscription to your newsletter and you think, “I’m such a fool, this will never work. People hate me.” You see a news headline predicting growth for your industry and you’re all, “It’s a sign! I’m on the right track.” You log on to Facebook and see someone doing exactly what you do but making beaucoups of cash and you fall into despair. “I’m such a fool, this will never work. People hate me.” Seriously.

It seems you are only as good as your last email or phone call. Don’t worry about it. These thoughts are only meaningful if you believe them. So when despair dawns (for the zillionth time), try to say something like this to yourself: “Oh, there’s that thing again that is pointing out to me how deeply I long for success in fulfilling my mission. I long for it so much that I’m incredibly sensitive. But every other time I’ve had such thoughts, they’ve eventually gone away. I’m going to assume that this current batch will too.” And when great hope arises, try for a mindset akin to this: “Things look awesome and I’m so excited.” Yay Cheering Back Slapping Celebrating Jumping Up and Down Congratulating Self for about 60 seconds. Then go back to work and enjoy how much you love the added energy that comes from faith in yourself.

PS If you have a book for sale on Amazon, never read your reviews. EVER.

3. Get away from your desk. I can be having the most down-in-the dumps kind of day and then go for lunch with a friend whereupon I return to work vastly energized. Even if you don’t talk about work, taking time away from your (necessary, useful) focus on yourself creates perspective. When you’re on your own, it’s very easy for that perspective to becomes twisted. I often say to my husband that my main job is managing my own moods. Connecting with others for a meal, a chat, a walk, a yoga class is more stabilizing than anything.

And of course, don’t be afraid to hide under the covers from time to time. We all do it. I might be doing it right now.

*Special thanks to Seth Godin for continual reminders and encouragement. If you’re making the leap to working for yourself, his books and daily newsletter are a must.

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