The Joys and Perils of Working for Yourself

I’ve been working for myself for the past 5 years. During that time I have served as an advisor and VP to an incredible Mongolian CEO and his tech startup, started and led a charitable foundation, did consulting work while completing grad school, served on several nonprofit boards, started my own company, worked with another startup, survived a complete layoff, and been a full-time entrepreneur. I’ve made more each year than the year before, starting from a solid Peace Corps salary of $250 a month and going up from there. I’ve also learned a ton (and not always the “Yeah, this is fun!” kind of learning, often the “Yikes…this hurts” kind of learning).

With that in mind, I’d like to share some things I’ve learned the hard way so you don’t have to. On the spectrum from Yeah! to Yikes, I will try to keep this essay on the Yeah! side.

Here are 5 tips on how to maximize joy and minimize the perils of working for yourself in our wild and exciting world:

1. Notice That Everything Has Changed. For a long time there has been a simple prescription for success: go to school, study hard, graduate, work hard, be loyal, get in debt, save up, pay off debt, retire and chill out. That model worked for decades but now not so much. Degrees don’t guaranteed jobs. The average stay in a company is more like two years, not ten. And more people work for themselves than ever before. Further, the idea of delayed enjoyment of life through retirement is less appealing. People are living simpler, being more creative, self-reliant, entrepreneurial and focused on work-life balance. We live in one of the most creative times in history and it’s a great opportunity to rethink how you are making a living and (more importantly) how you are making a life.

2. Get Clear on What Success Means to You. It’s easy to fall into the trap of doing what other people expect of us, to try to please people and follow a set path. It’s a lot harder to follow your own voice, say no to things and create your own path. It’s possible though, and it’s worth it. The most helpful first step I’ve found is to get clearer on my values and what success looks like for me. I’ve memorized my top 5 values (in order) and loved the process so much that I created a simple Uncovering Your Values worksheet which you can download here for free.


3. Don’t Run Scared, Run Experiments. One way I talk myself out of things is by overthinking them. I see the end product in my head and it’s so big and perfect that it seems impossible and I don’t even start. In my better moments however, I just think “Why not?” and just start with something small. I didn’t picture this whole essay for instance, I just started with a title. Then an outline. Then added sentences. Then it was done. I ask myself, “What’s the next little step I can take to experiment toward my new fun idea?” Derek explains this concept really well here (it took him from a one-click website to a $22 million dollars which he then gave away). The first time I sold my guide online and someone paid me when they didn’t have to, it was amazing! Now it happens all the time, but I had to start somewhere.

4. Take Care of Yourself. As they say, all work and no play leads to a nervous breakdown. And probably 50 extra pounds. Exercise is super important, especially when you are too busy to exercise. Research has shown that not exercising is the same as taking a depressant. Yikes. No thanks. Pick something you love and make it a regular thing. Get creative and mix work and play, hike and talk, go on walks for meetings, or bike and play video games like this guy who lost 135 pounds. I own this bike and love it.

5. Create an Advisory Board. Being an awesome entrepreneur (an awesomepreneur if you will) can be lonely. When I work at home or sit in the coffee shop writing posts like this, it’s easy to get lost in my own thoughts. Dreamers need to stick together. I have a short list of people who inspire me and I can call anytime to talk about just about anything. I love them to pieces and each one of them is priceless. Start with one person you love talking to and go from there. Don’t have one yet? Send me an email.

That’s it for now! I will share more tips as time goes on, but those are a fun place to start. In the spirit of experimenting, I’m also starting a video series for Awesomepreneurs, so I look forward to sharing those with you.

In the meantime, I wish you the best in your own entrepreneurial adventure whenever you may be!