A letter to myself after five years of self employment


Dear Me on July 16th, 2009:

I am not you anymore, but I remember what it was like. I still see you so clearly. You are laying on the sofa with a cold rag on your forehead, sobbing. Hyperventilating. You have just rather unceremoniously quit your stable, well-paying job to start your own business. You have $1600 in savings, and that’s not enough to take care of your responsibilities for any length of time. You have no backup plan.

There’s so much I want to tell you. So much I wish someone had told me.

The first thing is this: It’s still hard. You’ll still get exhausted and cry and feel like you’re doing everything wrong, even when you’re not. Other people will often make it look easy, and you’ll always admire that but never relate. On the other hand, people will sometimes tell you that you make it look easy, and you’ll love those people, but suspect they are a little crazy, or just being polite. (Still, say ‘thank you’ and offer something encouraging.)

The second, and perhaps most important thing: It gets easier. It gets so much easier. Eventually you will stop thinking that quitting your job was stupid-brave and come to believe that it was the absolute smartest decision. You’ll learn so much the next few years, and every single thing about your life will be different as a result.

You will initially supplement your income by nannying, by taking a (fortunately short-lived) shady website maintenance gig, and with a part-time development job. Don’t feel ashamed to not be standing on your own yet. You’ll get there. No use starving in the meantime.

You will come to understand the ebb and flow, and not only plan for it, but embrace it. Then the ebbs will cease — because what you worry about will find you, but what you trust will find you, too. I wish you would learn that lesson early. Don’t be afraid. All fear has ever done is hinder your progress. State your goals, believe in them, make them happen. That’s never failed you – not once.

Make your goals big for that reason.

You will find yourself on track to earn your first six-figure year, but as that December ends, you’ll fall $3,000 short and you will grieve. Heavily. As though $97,000 makes you a complete failure.

You will think in black and white this way often. It’s not good for you. Stop doing it.

You will far surpass your income goal the following year, partially just to prove to yourself that you can. But you will be tired and you’ll re-evaluate, and that’s the smart thing to do.

You’ll discover that there is more than one way to be successful.

You will find out firsthand that there are a few things that you can’t just “wing”, and one of those is taxes. Before that, you’ll underestimate one year and have to start a payment plan with the IRS. After months of torturing yourself with shame, you’ll learn that almost every business owner you admire has done the same thing. You’ll caution others not to do the same thing.

You will recognize the value of being vulnerable in business. You will see that we’re all in this together, and there’s no need to keep your cards close to your chest.

You’ll understand the importance of community, and that there is no such thing as competition.

You will make mistakes and be better for them. You will experience the difference a heartfelt apology can make from either side. Be humble when you mess up, and gracious when someone else does.

Don’t get me started on boundaries. (Okay, just this one thing: figure out what yours are. Soon. Stick to them. Be kind about it.)

You will work with truly, truly amazing people and many of them will remain good friends long after their initial projects end. They will change your life, and they will tell you that you have changed theirs. You will rejoice together when they land that contract, and cry together when they get divorced or lose a loved one. You will often feel that the process of creating something together is more than the sum of its parts, and that will fuel you. That will be the stuff that gets you through the patches of 15-hour days (which will almost always hit in April, for some reason). You will start to cultivate those relationships. Clients will tell you they hired you because they felt it in their gut, and those will be the best connections. (I know that sounds a little kooky now, but you’ll see.)

You will realize that any knowledge you possess today is just the foundation for everything you’ll need to learn tomorrow.

You will spend the first two years learning how to be a small business owner, the next two years basing all of your priorities on being a small business owner, and the year after that learning how to be more than just a small business owner.

You’ll start making art again, exercising again, and going on retreats. You will learn to take weekends off, but it will take a long time. You may not ever learn how to take a vacation. You haven’t yet, anyway. Get your shit together. (I didn’t say this was a love letter.)

It will always be hard, but in truth, you will love it more than anything. It will be the best thing you’ve ever done — the most challenging, the scariest, but definitely the most fulfilling.

And, you know something? Five years later, that $1600 will have never left your savings account. You will have never missed a rent payment. That cold rag was for nothing.

I hope you’ll pause to celebrate before moving on to the next thing on your to-do list. You’ve done a great job. Keep going.

Me on July 16th, 2014

10 thoughts on “A letter to myself after five years of self employment”

  1. I just adore you! Gut feels are the best feels.
    For the record – no flatterypants or crzyjuice in site πŸ™‚

  2. I love this so much! I’m so glad that I have been there for part of your journey as a client and (what I consider at least ;)) a friendship as well – you are amazing at what you do, lady!

  3. Loved loved loved this. I can relate to so much of it. You are so right about taking a moment to celebrate before moving on to the next item on the to-do list. That, I need to work on!

    Thanks for sharing and inspiring!

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