Looking for Debbie's books
and her work with teens?
Click here

My-deskOn this day in February, I’m thinking about the 33-year-old woman I was ten years ago, having just handed in my notice as a development exec for Cartoon Network with a dream of following my call to empower teen girls and young women and blend it with my love of writing. I nervously set out to be my own boss, set my own hours, work by the pool if I wanted to (we lived in So Cal at the time), and finally create a career that was ultimately fulfilling, where there was no separation between “work” and my “creative passion projects.” I didn’t know what it would look like, or where the gigs and money would come from, but I knew I had to step off the cliff of safety to find out.

Ten years later, I’m sitting in my home office in Seattle reflecting on the roller coaster journey of the past decade. In many ways, I’m not where I thought I’d be, and in others, I’ve far surpassed what I believed was possible. But one thing I know for sure — I’m so glad I took that leap.

To mark this anniversary, I’m looking back at what I’ve learned about the creative entrepreneurial life; both things that fall into the personal self-discovery category and things I think probably apply to anyone who chooses to follow their own path. Here are my top 11 takeaways:

1. It’s okay to not know where you’re going. I had no clue what my self-employed career was going to look like — all I had was a big-picture dream, a lot of tenacity, and the scrappiness to piece together a living using my writing and communication skills. Making it work has been difficult, exciting, and probably the hardest, most fulfilling thing I’ve ever done. It required (and continues to require) a boatload of trust. That trust is what gets me through the hard times.

2. I am actually an introvert. I love people, I love social time with friends, and I can do well in a team work setting, so my whole life I’ve assumed I was an extrovert. But over the years, I’ve realized how much I absolutely relish working, and being, alone. Quiet time by myself has become the key to not only my professional growth and creativity, but my sanity. Working alone isn’t for everyone, but I’ve discovered that it absolutely is for me.

 3. Community is key. Although I love working alone, the support of other self-employed peers — freelancers, consultants, entrepreneurs — has been a critical part of my growth. My community of like-minded souls is made up of people I’ve collected over the years through conferences, classes, listserves, and more, and is where I turn to for advice, insight, and mentorship. Without these awesome peeps, I don’t know if I would have the courage or confidence to do my thing.

4. Self-employed and working from home does not equal “available to do favors for everyone else:” I don’t know of a work-from-home self-employed friend who doesn’t get calls from friends or relatives asking if they could do them a favor — pick so and so up from the airport or watch their child on an early dismissal day because they can’t get off of work. Is one of the benefits of being self-employed the fact that we often have more flexibility in our schedule? Definitely. Does that mean our work time is any less sacred or important? Definitely not. Learning how to set boundaries was hard and sometimes pushed me way outside my comfort one, but it’s one of the most important lessons I’ve tackled.

5. You’re worth investing in.  I spent many years thinking I couldn’t afford to spend money on myself and my business, but I’ve learned that the truth is, I can’t afford not to. Businesses invest in their employees, and solopreneurs should do the same, whether its investing in conferences or continuing education or services like website design and marketing. The best part about creating a job you love is you get to design it however you want. So why not focus on doing the things you love to do and are good at, and find and pay for support around the areas that aren’t your strength?

6. I don’t “have to work” — I “get to work:” I still sometimes can’t believe I get to make a career out of doing what I love. I work many more hours than a lot of people I know with traditional full-time jobs, but it doesn’t feel like work. It’s what I love to do. It’s ick-free. And I feel like the luckiest person that I get to do it.

7. Solo lunch dates are a necessary indulgence. Because I can, I usually eat the same thing for lunch at home every day (Wasa crackers, turkey, cheese, and a green smoothie). It gets old, and I started noticing I was listening to my husband’s description of his lunches out in downtown Seattle with envy. “Must be nice,” I would mutter until I realized that I could take myself out to lunch, too. Doing that every one or two weeks has become a treat I look forward to, and feeling like I’m worth the occasional indulgence is good for (home) office moral.

8. Run, walk, or exercise every day. Getting out of the house for a run or an exercise class isn’t an indulgence — it’s part of staying healthy; mind, body, and soul. Self-care is paramount to any self-employed person, and deserves to have a permanent place on the schedule. A good rule of thumb? The busier or more stressed you get, the more vital the exercise is. Make the time for it, no matter what.

9. Napping is part of the job. I believe in guilt-free napping on an as-needed basis. I know I’m not alone here — Google, Huffington Post, and many other companies have official nap rooms in their offices. For this self-employed gal, napping when I need to (I take 30-minute naps probably once or twice a week) is one of the biggest perks of the job.


My furry muse, Baxter

10. Flexibility is a survival skill. Over the past 10 years, my work and career as a self-employed person has evolved, just like I have. I set out to be a fulltime writer, but today I also teach, coach, edit, consult, and more. Being willing to suck, accepting that failure is part of the ride, and being flexible enough to go with the flow of where the work and energy is has helped me adapt my business to the changes I’ve gone through as a woman, wife, mother, and creative.

11. Looking back can be helpful as you look forward. When you’re self-employed, there’s no boss to give you a promotion or raise, or to send around an email to the rest of the office to call out something great you did. It’s important to reflect on your achievements, acknowledge what you’ve created, and celebrate both your victories and your failures. You might have a success wall in your office, or keep a notebook with clippings from your major moments. Whatever you do, find a way to notice the important work you’re doing. It will fuel you as you continue growing your business into whatever you want it to be.

In that spirit of reflection, I’m closing this post with a summary of my past 10 years as a solopreneur. I can’t wait to see what the next 10 years brings!

Number of books I’ve written and published: 6

Number of book proposals I pitched but didn’t sell: 8

Number of books I’ve edited: 6

Number of articles I’ve written for print or online magazines: 125+

Number of TV shows I’ve pitched: 2

Number of TV shows I’ve sold: 0

Number of workshops and speeches I’ve given: 35+

Number of blog posts I’ve written: 262

Number of radio and television interviews I’ve done: 42

Number of corporate clients I’ve consulted or freelanced for: 13

Number of times I’ve redesigned my website: 7

Number of classes I’ve taken: 10+

Number of classes I’ve taught: 10+

Number of clients I’ve coached: 34

Number of writers I’ve helped with their books or book proposals: 19

Number of conferences and workshops I’ve attended: 11

Number of cities I’ve lived in: 2

Number of naps taken: Too many to count

Number of children I’ve had: 1

Number of vacations I’ve taken (a week or longer):  32

Number of pairs of running shoes I’ve gone through: 40+

Number of notebooks I’ve gone through: 27