You Know You’re a Solopreneur When…


Early one Saturday morning in February, after a day-long One Woman Shop strategy session the day before, an idea-inspiring Google chat was sent:

“You know you’re a solopreneur when… you have an idea for an e-course on Friday night, and by Saturday morning your Google Doc outline is at 12 pages.”

(That’s how we roll at OWS.)

In that moment, it hit us: how many times a day do we do things that are so recognizable to every other One Woman Shop running a solo business, but completely foreign (and slightly nuts) to everyone else?

For the next few days, we went back-and-forth non-stop, sharing our “You Know You’re a Solopreneur When…” moments. (Side note: YKYASW doesn’t make for the best acronym.)

Then, we opened the floor to our fellow One Woman Shops via our mailing list, Twitter, and our members-only Facebook group -- and the responses came flooding in.

Sit back, relax, and enjoy, fellow solopreneur -- here are the things to which only a One Woman Shop on the crazy, ambitious, up-and-down rollercoaster that we call solopreneurship can relate. Prepare to laugh, nod in agreement, and maybe even cry a little -- but rejoice that it’s not just you. We’re all in this together. (Cue High School Musical.)

You know you’re a solopreneur when... wake up in the middle of the night with a brilliant idea and must start working on it immediately. Even if it is 3am.

...your best ideas come in the shower or in your dreams -- then you struggle to remember all of the genius details when you’re back at your computer. love the concept of outsourcing but are having trouble letting go of your baby.’ve called your business your baby.’ve referred to your “online business friends” way more than once and have to explain to people that meeting up in person really isn’t gonna be weird.

...your significant other or best friend becomes your unofficial business consultant -- whether they want to be or not.

...terms like “solopreneurship,” “passive income,” and “list building” are part of your normal vocabulary -- and often provoke blank stares from your family and friends.

...the prospect of leaving your house both thrills and irritates you.

...snow days no longer exist because your studio or office is your home. (Oh -- and weekends and holidays aren’t a guarantee, either.)

...your yoga pants collection outnumbers your dress pants, putting on jeans counts as getting “dressed up” for the day, and the thought of dressing in business casual clothes is pretty darn exciting (as long as it’s not too often). have a call at 2pm and your voice cracks when you get on Skype... because it's the first time you talked out loud that day. (Thank goodness it’s not a video chat, because… hair.) walk into a cafe and immediately check for wifi and outlets. end up eating breakfast and lunch in that same cafe because you can’t drag yourself away from work long enough to relocate.’ve unintentionally skipped lunch on more than one occasion -- and not realized it until 3 or 4pm. “hold it” for way too long because you want to finish “just one more thing” before stepping away, even for a two-minute bathroom break.’re both happy and overwhelmed by the constant flow of new ideas you have (and, of course, there’s a Google doc or Evernote dedicated to each and every one).’ve spent hours -- when you should be working -- googling “how to be more productive” and “productivity tips.”’ve listed the pros and cons of about 50 different e-courses, conferences, and coaching programs and talked ad nauseum about the need to “invest in your solo business.” commonly debate MailChimp vs. Aweber, WordPress vs. SquareSpace, and Canva vs. PicMonkey as if you have a personal stake in them. can recall the HEX codes for the colors in your brand faster than your own social security number. love seeing how other solopreneurs structure their days, and think “yes! I’m not the only one who drinks four cups of coffee per day.” whip out dozens of pages of content in a few hours when you’re inspired, but it takes days to write a 500-word blog post when you’re not.

...the last day of the month means wrapping timesheets, sending out invoices, and checking in on your books.

...the UPS/FedEx person knows you by name.

...your first thought when you meet someone who has never used Skype or G+ Hangouts is: "How do they meet with people?” think in multiple time zones and are rarely 100% sure of what day of the week it is.

...paying quarterly estimated taxes makes this whole business thing feel like it’s not worth it...until you realize you can go to a 10am yoga class or even work from anywhere if you want. think, “I would NEVER date a solopreneur. We’re crazy!”

But perhaps the thing that’s most indicative of being a solopreneur?

You no longer dread Monday mornings.

And that, fellow solopreneurs, is how we know this solo-business gig is all worth it.

What’d we miss? Let us know in the comments below!

A huge thank you to Razwana Wahid, Susan Shain, Jennifer Lopez, Sierra Elmore, Jennie Mustafa-Julock, Katie Radke, Jennifer Vitale, Sara Moss, Martina Weiss, Julia Sydnor, Jessica Maceda, and Faye Kirwin for contributing!

  1. Kim says:

    Yup. I have done all of these things! I made the transition from solopreneur to boss 6 months ago and it was a big transition—but so worth it for my business’ growth.

    • Tai says:

      That’s awesome, Kim! I made my transition July of last year. Scary but exciting. I think I’m spoiled now!

      • Thanks for commenting, ladies! Congrats on making the transition. It’s exciting, scary, and so much fun! And it’s always nice to have some communal things to laugh at 🙂

  2. Kendra says:

    HAHA! I love this!

  3. Tai says:

    All I can say is “right on!” I was just thinking this morning how badly I do NOT want to go back to a 9-5. And I make it a game to see how quickly I can scan a coffee house or public library room for outlets with minimum neck turning. It’s like eyeball workout!

  4. Thanks for sharing this awesome post. All the points above have happened to me at some point over the last year. I’m new to this whole solopreneur thing.
    What about you know you are a solopreneur when…. you will take your last money and buy a new theme because your website doesn’t look perfect.

  5. Christine says:

    OMG this is all SO true! LOL! Thank you for literally making me laugh out loud. I needed that!

    And I JUST finished yet another article debating MailChimp and Aweber – LOL! And I JUST took a look at Canva wondering how it’s better than Picmonkey!!! 🙂

    I would add:
    You’ve thought about changing your business name, domain name, and/or web design at least 3 times today.

    BTW, I recently stumbled upon your website, and I’m so glad I did. Nice to know I’m not alone – especially when I haven’t seen anyone outside the virtual world (besides my husband and kid) for days. LOL!

    Hexcode D05353

    • Christine (or should I say Hexcode D05353?) – 🙂

      Thanks for commenting, and for the addition to the list. SO true.

      We’re so glad you found OWS. You’re definitely not alone!

  6. Caroline says:

    haha yes! Love this! I was up at 4am this morning and had to start working because my mind was racing.

    • Caroline — I always say I’m going to stick to a routine, but when early morning inspiration hits or a late night rush comes, there’s just no avoiding it. Cheers to loving your work! (And coffee + naps! 🙂 )

  7. Kathryn Hall says:

    This is hilarious and so true! My poor boyfriend has to put up with me having mad hair most of the time because I have no reason to leave the house. So glad to hear it’s not just me!

  8. Matea says:

    Haha this is brilliant and so true! :))

  9. Stacy says:

    These were really great, and honestly the timing was way too perfect!!!

    “…you can recall the HEX codes for the colors in your brand faster than your own social security number.” — Way too true!

    “…you’ve spent hours — when you should be working — googling “how to be more productive” and “productivity tips.” — This one made me literally ‘LOL’. I have probably spent more time the last 2 days learning “how to be more productive”, while not much work has been done at all! 😉

    I really appreciate all of these posts and comments. I know that this post is a year old, but I still felt the need to speak up and say Thank you!

  10. Karin says:

    Oh, when you look around at 2 am in the morning, because you just have to finish that last blog post perfectly, and wonder where everyone went! Actually, my husband has recently taken to turning the internet off at midnight to encourage me to bed, I am such a nightowl ?

  11. Wendy says:

    Oh my! I relate to many of these, ‘leaving the house both thrills & irritates’ ‘go straight for the wifi & plugs at cafe’s’ My husband took me out to lunch today and I was impatient to get back home! I have just found OWS this morning through Instagram and it’s great to be reminded that what I think is me being overly obsessive about my business is actually pretty normal!

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