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.

  • http://www.marsdorian.com/ Mars Dorian

    Nice Jenny, lots of these tips actually help me as well, because it makes me re-consider my current choices and options. 
    I’d luv to go to the conferences, but most of them are overseas, and the ROI isn’t grrreat enough to justify that kind of investment !
    BTW – 500 bucks for health insurance ? Damn, that’s pricey. Do they share their stocks of gold with you ;) ?

    • http://www.lifeaftercollege.org jennyblake

      Thanks Mars! Yes – I’d imagine conferences overseas for you would be totally cost-prohibitive and not worth the investment…Skype is good for now, until I Luv Empire blows up and becomes world-famous! Then people will be flying you out :) 

  • http://www.wegrowmedia.com Dan Blank

    Jenny – this is SO useful. I think overall it shows you the true life of an entrepreneur: that you have to think about a wide range of critical issues CONSTANTLY. All of this stuff rattles around in your head 24 hours a day. And for most early entrepreneurs, you work from home which means that in some sense, you always feel the opportunity (and pressure) to work on one of the many exciting projects you are building. 

    Thank you so much for sharing this!

    • http://www.lifeaftercollege.org jennyblake

      Thanks Dan! Ahhh, you make SUCH a great point that there’s such a wide range of issues that we juggle every single day. I totally feel you on working from home too — I often feel like I should be working, and work waaay later than I should be (just as I was when I had two jobs!). I look forward to drawing more boundaries once I finally launch MSH and get out to NYC — but I know it’s going to take a LOT of discipline.

      Thanks for your great comment — have a wonderful week! 

  • http://www.rulebreakersclub.com Courtney | Rule Breaker’s Club

    So helpful as I embark on my own micro business venture!

    It’s nice to see someone embracing fear + going for the long-term instead of worrying about if it’s all going perfectly RIGHT NOW. 

    You are going to succeed 10 fold because of your courage + determination! 


    • http://www.lifeaftercollege.org jennyblake

      Thanks so much Courtney, and congrats on launching your own micro-venture!! LOVE that you’re taking a long-term view. Thank you so much for the kind words — right back ‘atcha, girl! Thanks again for stopping by :)

  • http://justicewordlaw.com Justice Wordlaw IV

    Congrats on your development of MSH. I am excited to see how it develops and when you release your product as well. You don’t know or understand how much you spend via airfares until you really start going to events across the U.S. I started using most of my reward points via my bank and c.c towards the hotels and new suits via @Burberry:twitter for most of the events. Great post and congrats

    • http://www.lifeaftercollege.org jennyblake

      Thanks Justice!! It’s nerve-wracking but exciting — been working on it all summer and getting ready to release to the world on September 13. It means so much that you’re interested in following the progress! Hope you had an awesome weekend — thanks so much for commenting and for all of your support :)

  • Priscilla Taylor

    Thanks for sharing these tips Jenny! I appreciate your honesty because sometimes we see the “final product” and getting there isn’t always simple and easy. 

    • http://www.lifeaftercollege.org jennyblake

      Thanks Priscila! I’m big on sharing the process not just the final product…because that’s where all the learning is! So glad that it’s helpful for you — have a fabulous week! :)

  • Sorakainomori

    This has been so helpful in determining what step I need to take next. I was hoping to start a second job this week, but it got cancelled, so my funds aren’t as guaranteed as they used to be. But now I have all this spare time that I’m hoping I can get started on my side hussle projects.

    • http://www.lifeaftercollege.org jennyblake

      I’m so glad this post came at just the right time! Second jobs and side hustles can be unpredictable, but it sounds like you’ve got lots of juicy ideas cooking…best of luck with everything! 

  • http://yourkickasslife.com Andrea

    Jenny! Great post and one question: Which do you think is the best conference to attend for us coaches? 

    • http://www.lifeaftercollege.org jennyblake

      Thanks girl! Tough question…I don’t know! I LOVE SXSW, but WDS this year was a very close second — and LOTS of self-employed coach types there. Have you heard anything about the CTI conference this year? I wonder how that was…

  • Al Smith

    Thanks for the post!  I really like how you have been so honest and straightforward about your experiences.  Many people out there suggest starting a business is the silver bullet to the ills of life, howver that is not necessarily the case.  It is truly hard work.  Although I must say, it is certainly possible. 

    • http://www.lifeaftercollege.org jennyblake

      Thanks Al!! Hard work indeed, and it’s really important to me to share the ups AND downs so that people have a sense for what it involves. Thank you for your kind words — it’s great to know that you value the straightforward approach. Have a wonderful week ahead, and thanks so much for taking the time to comment!

  • Kim

    Thanks for the words of wisdom.  I got laid off  after Christmas and went back to school to geek up my skills and forge a new path away from the cube farm.  This is a great vision of what the next steps are going to be like.

    The first thing I learned:  COBRA is a total rip-off.  Save yourself a LOT of money, and get an individual plan.  My health insurance company (Group Health) has plans ranging from $70-300 per month, and it was easier than I thought it would be to sign up.

    Good luck, and thanks again!

    • http://www.lifeaftercollege.org jennyblake

      Thanks Kim! Sorry to hear you got laid off…sometimes change chooses you and you have no choice but to adapt. Amazing that you’ve gone back to school! Best of luck to you as well — thanks for taking the time to comment!

  • http://www.thinqaction.com Antonio Neves

    So happy to have found your site. I really dig this one: “What gets measured gets managed.” It goes along with goals without feedback are useless. Thanks for sharing your journey and welcome to NYC. We’re on a similar journey in our work and would love to break bread. Cheers!

    • http://www.lifeaftercollege.org jennyblake

      Thanks so much Antonio – so happy you found it too! Very nice too meet you, and looking forward to keeping in touch. Coffee in NYC once I’m settled (October-ish) would be great!

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  • http://www.gettingonlineincome.com Lucy

    My walls are filled with my “PLAN”, I’m going to blogworld, I have met some people that inspire me to continue on the field, and thankfully I have a good job.

    I feel stressed but lucky.

    • http://www.lifeaftercollege.org jennyblake

      Thanks Lucy! That’s awesome that you’re knee-deep in planning mode — best of luck with everything..not that you’ll need it! :)

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