20 Lessons from 2 Months of Solopreneurship (Part One)

I’m writing today from a place of deep gratitude. I was one of two keynote speakers at the first annual 20 Something Blogger Summit this past weekend in Chicago — three incredible days of ideas, connections and reunions with friends new and old. Despite my nerves about living up to keynote status (this was my first), the speech went off without a hitch.

I have the audience to thank; it was without question the best group I’ve ever spoken to; their energy, compassion, attention, humor, and presence lifted me up and made my job easy. By the time I sat down, I had 200+ @replies on Twitter, and though I didn’t get a chance to respond to each one, I’d like the attendees to know how deeply moved *I* was. Thank you so much. Big thanks are also in order to Derek and A Squared Group for putting on a killer event, and for believing in me.

Below is a two-minute video snippet from my speech (thank you Stephanie Florence for capturing this!), in which I talk about the importance of community and the impact Michael Ellsberg had on my decision to leave Google after only knowing him for one week. I’ll be sure to post the full keynote video as soon as it’s available!

Welcome Escape from Cubicle Nation Readers!

I’m excited to be featured today in the Side Hustle & Flow series on Pamela Slim’s – my friend, mentor and Internet Auntie’s — blog, Escape from Cubicle Nation.

For several years now, Pam (and her work) has been a guiding light for me. I showed up at her first Escape workshop in 2009 after devouring her book, debating whether to stay or leave Google. I sat in the back and didn’t say much. I was beyond scared and confused.

I kept reading her blog and the side hustle series, watching her in admiration as a model for how I’d like to run my business, wondering when I’d have the guts to go out on my own and tell my story like her other courageous readers had.

Two years later, I’m proud to report that it’s my turn to hopefully show others that one day they too can make the leap if that’s what their heart is telling them to do. If you’re new here, get caught up with I’m a Free Agent: From Six Figures to Suitcase and Free Agent Part Two: Big Decisions + Very Real Fears. 

20 Lessons Learned in 2 Months of Solopreneurship (Part One)

The last two months of solopreneurship have been some of the happiest of my life. I’m in love with my newfound freedom! But they haven’t been easy, and I’ve had to make adjustments every single day as I learn what works and what doesn’t for my life and business.

I may share more detailed numbers later, but for now: I broke even on income to expenses in July, then in August the lion’s share of my projected income (mostly coaching and speaking) got cancelled or postponed. It’s been tough, but I’m okay with that; I consider this a building month as I get ready to launch Make Sh*t Happen, my new course, in a few short weeks.

I feel a little silly writing this post because more seasoned entrepreneurs may be reading it thinking, “Oh just you wait!” or “What does she know?” but nevertheless, this is a snapshot of where I am in my learning two months in.

1. Fears are so much smaller on the other side. Prior to my decision to leave, my fears rang in my ears so loud I could barely hear myself think. It was as if my inner critic stood on a soapboax shouting through a megaphone, commanding me not to shake up the status quo. Now that I’m on the other side, my mind is quiet again. Despite losing almost all of my projected income for the month of August, I am not afraid. I am motivated to act. As Joan Baez said, “Action is the antidote to despair.”
2. Readjustment takes time and energy. Going from the structured, fast pace of a 9-to-5 job to total wild-wild-west freedom is an adjustment. I grossly underestimated how much mental and physical energy making such a MASSIVE transition would take. I felt very tired for the first few weeks as my body finally got a chance to rest after working so hard on my day job and side hustles for so many years.
3. The old adages ring true: get comfortable being uncomfortable, and the only certainty is uncertainty. This has been my biggest mental shift since striking out on my own. Going from a steady (very healthy) paycheck to….total uncertainty…has been a major adjustment. As a solopreneur, especially in the beginning, you’ve got to get comfortable not knowing exactly where every dollar will come from. Work comes in, work gets canceled. You sell things and it works; you sell things and they flop. Developing semi-passive income streams takes time, and there’s nothing passive about the process. One night I went to bed with a knot in my stomach about how I’d pay my credit card bills. The next day, in one hour, I had sold $5K of business. The next week, it was gone. You’ve got to get comfortable (or as close to comfortable as you can) riding that wave without freaking out.
4. On that note, NEVER count (or spend!) your chickens before they’ve hatched. It’s ridiculously easy to do, and it is definitely not fun to dig out of. Desperation isn’t attractive when dating or selling.
5. Routine is king. For the first month my productivity on any given day was a total crapshoot. On some days I would wake up rearing to go, and on others you couldn’t pay me to pry myself off the couch. Because I was lacking routine, I was at the whims of what side of bed I’d wake up on. As Jonathan Fields shared at WDS, some of the most successful creatives have very structured lives, even if their actual creative time is very free-flowing. This predictability allows them to manage the rest of their lives with greater ease, thereby focusing their best energy on their creative work.
6. Health and fitness is queen. I just finished a 21-day cleanse with no caffeine, alcohol, dairy, wheat, refined sugar, or red meat. I knew I’d physically feel better by the end of it (light years!!!) but I had NO idea how significantly it would impact my business. I am infinitely more creative, happy, and productive every day. I’ve gotten more done in the last three weeks than in the last two months! I’ve finally re-prioritized exercise too — I run every morning for 20 minutes before doing anything else, and I try to go to yoga 4 times per week. Centering my day around exercise — putting it at the very top of my priority list — is THE BEST thing I have done for my business since leaving Google.
7. Your community are your new co-workers. Just because you leave your job doesn’t mean you have to work isolated on an island. As I talked about in my speech and the video above, you have so much more support than you realize. LEAN IN to your community, let them lean into you; you have so many people rooting for you, especially those of you who have built thriving communities on Twitter, Facebook and your blog.
8. Run your business otherwise it will run you. Tackle 1-2 big frogs each day before you do anything else (h/t Brian Tracy). You’ll feel a sense of pride and accomplishment, and you won’t resent reactive things that come up later in the day because you’ve already made major progress. After my mandatory morning frog (the 20-minute run), I try to accomplish 1-2 things that will significantly move things forward, whether it’s a blog post, drafting a sales page, creating a newsletter auto-responder, or building the MSH course. Only later do I start responding to emails or taking calls. I also only take meetings on Tuesdays and Wednesdays, which allows me to eat many frogs on every other day of the week.
9. However, sometimes you need to start with quick wins. When I’m tired or particularly behind, opening my my inbox to answer email can feel like going in for a root canal. During moments like that, if I try to go after a big frog, I’ll get overwhelmed and not do anything at all. So I start with quick wins — emails I can answer in two minutes or less; tasks I can complete in 30 seconds. That gets me moving, and there’s a good chance I’ll dive back into the bigger stuff once I get going.
10. Building “entrepreneurial resilience” is like building a muscle; it takes practice. This is something my good friend (and high school & college classmate!) Alex Budak and I have discussed at length. Alex is an awesome guy who recently left his corporate gig to launch Start Some Good, which facilitates kickstarter-style funding for social entrepreneurs.
    In Alex’swords:

    “Especially as a first-time entrepreneur, the roller coaster that is starting one’s own business is intense.  The highs feel incredibly high, and the lows feel incredibly low. Simply recognizing that this is normal and to be expected was a huge step for me as I sought to strengthen my own entrepreneurial resilience.

    The second, and equally crucial step for me was surrounding myself with fellow entrepreneurs.  It’s amazing how easy it is, when isolated, to think that you’re the only person going through these ups and downs, but as soon as you share your struggles with others, you realize just how similar many of the issues are.  Just like you’d prefer to sit next to someone on a real roller-coaster, having friends alongside you to ride the entrepreneurial roller coaster makes a huge difference.  Oh, and as my friend Jenny told me, ‘It helps to just breathe, sometimes’ too.”

Stay tuned for the next 10 lessons later this week! In the meantime, what did I miss?

Have you experienced any of the lessons above,
either on your side hustle or full-time work?