Anatomy of 10 Years as a Solopreneur
On 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.
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
Reflections on the Death of a Hard Drive
Yesterday morning while brushing my teeth, I plopped down onto my office chair and turned on my computer. My plan was to check in on email and attend to a few things before waking my son up for school. But when I turned on my computer, I was greeted with a little circle with a line through it, set against a 27-inch backdrop of gray. No cheerful launch noise (in fact, no noise at all), no desktop wall featuring a picture of my son grinning from ear to ear atop the Brooklyn Bridge.
My harddrive was dead.
Thankfully, I’d signed up with an online backup system a few months earlier (BackBlaze) so I knew all of my documents and data were saved…somewhere. That helped me from dissolving into a frantic mess. But my calendar? Email folders? Who knows.
My hub, who doubles as my personal IT guy, was out of town, so I was left to figure this one out on my own. I called Apple, made an appointment at the store near me, and hung up, just as my now-awake son asked to see what a “dead computer” looked like.
I could tell I was stressed. My energy was anxious, and my son was picking up on it — not the way I wanted his before-school routine to play out. So I took some deep, deep breaths, and tried to focus on what I knew.
It was out of my control.
I could panic, or not — the outcome was going to be the same.
I didn’t have any deadlines this week where I needed to turn in a big deliverable (one that I likely would have been working on solely on my desktop).
Maybe it was a sign that I was supposed to slow down. (Um, probably.)
Maybe I needed to remember what it feels like to be really uncomfortable and out of sorts. (I remember now…thanks.)
Maybe this is the perfect opportunity to think about what actually has to get done and I’ll realize that a lot of the work stress I experience is self-generated. (Sometimes I push myself too hard to do too much all the time.)
Maybe my desk was in need of a good, deep scrubbing. (It was.)
This morning, I have my computer back. I picked it up last night and it’s sitting on my desk, daring me to turn it on. I haven’t yet though. I think knowing it all has to be set up again, knowing that likely I’ve lost some valuable info, and feeling a little anxious about doing something wrong in the data recovery process has kept me from pushing the ON button. I’ll wait until my personal IT guy gets home.
So today, you’ll find me reminding myself (frequently) that it is what it is. No worrying, stressing, or freaking out is going to change that. I’ll figure it out. I’ll piece things back together if I have to. And I’ll try to find peace in the fact that what’s gone is gone.
My friend, life coach Pedro Baez, often talks about the importance of riding the waves of life when they hit instead of panicking or swimming against them. Today I’m grabbing a board — I’ll see you out on the surf.
Feast or Famine
Feast or famine. For many of us in the world of freelance and/or self-employment, that seems to be the way things roll.
Even with the most deliberate business planning, we often find ourselves either scrounging for projects or with more on our plate than we can handle. We never know when we might get a call or an email with an incredible new opportunity, and that’s a reality I both love and struggle with. Struggle with because I like to know…like to have control. And love because those calls and emails always do come, and often with opportunities that are even better than I could have drummed up in my head.
To combat the feast or famine, over the past year I’ve been focused on creating more opportunities for my own business so I’m not reliant on waiting for people to come to me. But the interesting thing is, since I’ve been doing that, more opportunities from the outside world have been cropping up. Projects I’ve pitched in the past few years and never landed suddenly have new life. Other areas of my business that I’ve been neglecting are suddenly exactly what clients are looking for. And so my own personal business plan for 2013 — the one where I outlined what I was going to create and where my income was going to come from — is already on its 3rd revision. And it’s only February. (And I’m totally cool with that.)
If you watched this Sunday’s Super Bowl, you saw how quickly and powerfully momentum can shift. As a Ravens fan, I was blown away by the power they showed in the first half and equally so to watch how quickly San Francisco took back control in the third quarter. The game was the perfect portrayal of the mantra, everything’s changing, all the time.
So the challenge then is, how can we come to peace with the changes in momentum in our own business and creative lives? How can we mentally stay in the game and maintain optimistic and energized about our passion projects when they haven’t yet connected in the outside world? How can we stay in a place of trust with our own feast or famine?
- Keep creating. Instead of waiting for feedback or for the sale or deal, go back to the drawing board and work on what you want to create next.
- Let go of the outcome. Our projects have a way of finding their own path, often when we least expect it and frequently in a way we didn’t necessarily intend.
- Don’t panic. Don’t break your famine with fast food just because it’s the first meal that came along. Work on the projects that feel inspiring and/or connected to your passion or purpose.
- Find support. Build your community with other creators who can relate to the feast or famine syndrome, and lean on them for gentle reminders and confidence boosts when you need them.
- Be curious. Stay open to the possibilities of what’s next, even if you don’t know what it looks like or when it will happen.
- Be grateful. Appreciate your successes and failures, big and small, for their role in your life. Be grateful for your unique POV and creative outlook.
- Keep sharing. Your message is your gift to the world.
A Modern Day Identity Crisis
In my world, I talk with/work with many creative entrepreneurs, and one of the most common threads I’ve discovered is that many of us find it challenging to articulate what we do and who we are (present company included). And that’s a problem (and not a small one), since finding a way to be successful passion pursuers is often reliant on connecting with our tribe. So, what gives?
When I was in my early twenties, I remember wanting to be able to answer that question — what do you do? — simply and confidently. I was always slightly jealous of people who could just blurt out a response, no confusion or explanation necessary: I’m an accountant. I’m an advertising executive. I’m a social worker. I’m a veterinarian.
I did have a “real job” back then (I worked in video production for several different organizations) but I also had many other things going on that felt just as important, and actually more so, than my 9 to 5 gig — I was a graduate student, an independent documentary producer, an aspiring author, a workshop presenter for homeless teens.
For my entire career in the nonprofit and eventually corporate world, my day-to-day job was never enough, and I longed for the day that my work and my personal passions would be one and the same, when I didn’t feel as though I had to spend all my free time working on what I really wanted to work on.
Ten years ago, almost to the day, I took the leap to make that dream a reality.
Yet though my work and and personal passions are finally united, I still find myself grappling with how to answer that same question — What do you do?
More specifically, I’m not sure how to clearly convey who I am and what I’m all about so the people I want to work with “get” me and can find me.
Here’s what I do know, though. I don’t want to fit into a box. I’ve got a bunch of different areas of interest, expertise, and passion. I’m rebelling against the notion of having one clearly defined niche. I just want to figure out how to weave it all together.
My goal is that at the other side of this identity crisis I’ve figured out a way to more clearly connect with the people I want to serve and work with, and that I’m moving forward in my business in a direction that’s the most fulfilling, rewarding, and yes, even fun.
So, for now, I’ve only got the long, rambly answer about who I am from a business POV. I’m an author, I’m a speaker, I’m a content creator, I’m a consultant, and I’m a coach. I am equal parts passionate about helping teen girls and young women kick ass in their lives and supporting writers and creative entrepreneurs do their thing. I believe every person can make a difference in the world. I want to be part of that change. Every day.
It’s not all neat and tidy yet, but I’m starting to get there. And I’m starting to realize some of the “rules” around how to market and brand a venture don’t have to be true. Here’s my take:
It’s okay to have more than one “specialty.” If you have gifts to share, why shouldn’t you share them all?
Your “why” at the very core of what you do in the world is the most important thing to get clear on. Your “why” (check out Simon Sinek’s book Start With Why) is what will connect all your various “specialties.”
There is no one right way to market or present yourself. When in doubt, choose authenticity.
It’s fine to change your mind. And to grow. And to evolve. (It would be so boring if it wasn’t.)
You don’t have to get it all right before you start sharing your gifts. Figure it out along the way and share your process with others. It’s a journey…bring others along for the ride.
Fumbling Through
My post today is going to be a little different than my usual thing.
When I started this new blog a year ago, my promise to you was that I’d be completely authentic and let it all hang out. So, there’s no way I can sit down to write today without letting you know that I’m feeling extra challenged right now. Not challenged work-wise, but challenged life-wise.
As parents, my husband and I are struggling with knowing how to best support our son right now. He’s got some special needs that make him especially tricky to parent. (I wrote a guest post about what it’s like being his mom at Andrea Owen’s blog earlier this year.) Most of the time, I’m good with what’s going on. I’m a researcher, so I’ve read the books, I know the websites, I have the specialists lined up. I’m also a doer and a problem-solver, so I plow ahead and come up with plans, get everybody on board, and get to work.
But sometimes, like now, when my son is in the throes of a particularly lengthy and unpleasant regression, it’s harder.
And so I’m trying to figure out the how to balance it all. How to maintain my own self-care, how to meet my deadlines, how to tap into the creative joy and passion that drives most everything I do in my work life, while managing my energy with my son, being fully present for him, and staying grounded even when it’s raging all around me.
Though our son is 8, I still feel like I’m new at this, and as far as I can find, there’s no guidebook to tell me how to walk through what we’re experiencing at home. So for now, I’m going to keep fumbling through. I’m going to trust that things will get better (they always do) and give myself a break (I don’t have to figure it all out right now).
I’m going to find time to play more and find time to rest.
I’m going to work on letting go of the strongly held wish that things were easier (because they’re not).
I’m going to try to approach my parenting with the same creativity I put into my work and writing.
I’m sharing what’s going on because I think in today’s very public way of being and connecting through media like Facebook and Twitter, it’s easy to look around and think that everyone else is doing great…that we are the only ones going through really hard stuff. And that can hold us back from sharing, from creating, from finding peace in our circumstances.
And I think it’s important that we learn to be okay with being in this space.
It’s part of every human’s experience, in one way or another. I believe it’s all happening for a reason. I believe it’s where inspiration comes from.
















