20 Lessons from 2 Months of Solopreneurship (Part Two)

Can you believe summer is almost over? I’m shocked at how fast time is flying. It seems like just yesterday that I was hosting a Creative Day of New Years Genius and making big plans for the year, uncertain about where my book and sabbatical would take me.

I had no idea that just nine months later I’d be packing up my things to move to New York, self-employed, pinching pennies and researching everything from how to get health insurance to how on earth to sign and send in forms without so much as a scanner or a printer (though I’ve since discovered a super handy tablet app that does this!)

Earlier this week I posted the first 10 of 20 lessons I’ve learned during the first two months of solopreneurship. I’m sure there are hundreds more coming my way — and that each of the things I have shared will become even more real and important over time. You can also read more at the Side Hustle & Flow Series interview I contributed to Pam Slim’s Escape from Cubicle Nation earlier this week. 

20 Lessons from 2 Months of Solopreneurship (Part Two)

  1. No matter what business you’re in, you’ve got two priorities: learn about sales and marketing. Michael talks about this is his upcoming book — for most of us, sales and marketing are not things we learn in school, and yet they are vital skills for making a living as a solopreneur. I’ve been giving myself sales, copywriting and marketing boot camp with the help of brilliant friends like Andy, Jonathan, Michael, and Calise.
  2. Plan ahead for building months (as opposed to doing months). I’m “in the red” this month on expenses to income, but it’s largely because I’ve been working like a madwoman building out the Make Sh*t Happen course. I’m placing a big bet that people will sign-up; if it works, I’ll be relatively stable income-wise in Q4; however, looking back, I should have planned ahead more in July so that I didn’t have such a drop in income. If you know you’ve got a building month coming up, ask yourself if it’s okay to dip into savings, or whether you need to split your time between building and immediate sales-generating activity.
  3. Stay grounded in your long-term vision. I could be doing a much better job of this. I have a vision for where I want my business to be six months from now, but the next thing I’d like to do is plan how I want the JBE operation (aka my life) to look a year from now. It will make all of the micro-decisions between now and then much clearer (while still leaving plenty of room for adjustments and surprises along the way).
  4. “What gets measured gets managed.” This is a saying I learned from one of my favorite managers at Google. I had a really helpful call with Michael Bungay Stanier (of Do More Great Work) when I was starting out, and he told me about the monthly metrics he tracks. This will be no surprise, but I’ve set-up a tracking spreadsheet where I can see data for ~20 statistics related to my business (coaching clients, speaking gigs, monthly traffic, book sales, subscribers, etc) and the percent change month-over-month. Michael makes a great point that once you’re tracking, the real challenge is to figure out which numbers are actually useful/important; not every metric matters.
  5. (The right) conferences are major business boosters. I’ve attended five conferences this year (SXSW, BiSC, WDS, BBNYC, 20SB Summit), and at each one I’ve met new people, reconnected with existing friends, and learned a mind-blowing amount of helpful best practices from others doing similar work. If you can scrounge up the money, I think this is one of the best investments you can make.
  6. However, beware the many costs of travel. Trips — even ones I’m getting partially reimbursed for — can be shockingly expensive! Beyond flight and hotel, common expenses include cab fares, meals out, airport purchases, Internet on the plane (I fly Virgin everywhere), touristy activities, drinks with friends and shopping for clothes to wear at these events. I need to keep a really close eye on this in the future.
  7. Peer support is key. It might be your first launch, but you are not the first to launch. I’m excited and super nervous about launching MSH. For example: I’ve never written a sales page or set-up a payment system. No matter what you’re doing, talk with others who have gone before you on your big goals. Big thanks to Sean and Molly who have shared their tremendously helpful lessons-learned from their launches.
  8. Peer support and bootstrapping is great, but know when to hire professional help. Once you’ve reached a limit of what you can do on your own, it makes sense to hire professionals who can help in areas you are deficient (without going overboard); for example: a VA, an accountant, and web designer. I could have designed my website myself (I have the technical skills) but with nowhere NEAR the polish that Nina did.
  9. Be creative with how you structure your time. Focus. Maximize your best energy windows. When do you do your best work? Structure your days and weeks as best you can to optimize those windows, and know what activities recharge you when you hit energy dips. For me that’s getting out of the house and going to yoga in the afternoons, then I can work again when I get back.
  10. Monthly recurring expenses can add up VERY quickly. I had NO idea how quickly my monthly business-related recurring expenses would add up. Here’s a short sampling that DOESN’T include one-off software purchases (also very pricey): COBRA health insurance ($500), cell phone ($80), Dreamhost ($30), VaultPress Blog Backup ($15), AWeber Email ($19). Total: ~$700 — and that’s before adding in gym, yoga, rent, travel, food, etc. YIKES!

Bonus: #21. Despite the challenges (and the many more sure to follow), working on JBE full-time is still the most incredible, freeing feeling in the world. I haven’t looked back for one second. I feel like ME again. Or rather, like I finally have access to the best version of myself that I always knew was hibernating underneath the stress and uncertainty. I feel ALIVE.

Previous post:

Next post: