You know you're working for an entrepreneur when...


You know you're working for an entrepreneur when...

+ You feel like your boss is always changing her mind

+ You feel like you're an expert on everything from unclogging a toilet to mastering google docs (rainbow spreadsheets, hell ya!)

+ You started with a job description that was super specific but now you pretty much run the show

+ You sometimes stop to think, "Maybe I should be doing this myself so I can make more money!" 

+ You took a pay cut to do something inspiring and creative but now realize there's a grind to working for a startup the way there's a grind to ANYTHING in life. Thank god it IS more creative and inspiring then that thing you were doing before.

+ You roll your eyes a little when people tell you how much they "wish they had your job". (It's not as great as you think it is, Joanne)

+ There are mornings you wake up and don't have to be anywhere specific and you pause to remind yourself, "THIS is so worth it".

+ You get to make decisions that effect the bottom line of the company and that fuels you to be innovative and think outside the box.

+ You feel like your boss goes back and forth between being your bestie and an actual nightmare who wants to text about her "exciting new idea" at 10pm on a Tuesday. (I'm WATCHING THE BACHELORETTE!)

+ You check everything off your list and feel SO DAMN SATISFIED only to have a whole pile of new things to tackle an hour later.

+ You often feel like your boss hung the moon (goddamn she's inspiring!)

+ You often feel like your boss is super out of touch with what is ACTUALLY going on day to day 

+ You are 100% familiar with staff meetings in a hot tub at the gym or happy hour at your favorite bar. This is small business, yo! There aren't any rules!

+ You fantasize about corporate careers where you KNOW you would get that 401K and killer healthcare plan. (so putting dental care on my next vision board...)

+ You say, "Love you!" to your boss when you hang up the phone.

+ You wonder how she does it all. Like for real. HOW DOES SHE???

+ You feel like everything would crumble if you walked away. (Like she KNOWS she needs me.)

+ You have a sense of purpose that no other job has given you. You're making a difference. You're building something that aligns with your values.

+ You know "unlimited PTO" really means, "I can't afford any other perks so there's THAT at least" and also, "You're so obsessed with this job you'll barely take 2 weeks".

+ You feel bad for your friends who get up at 7am every day and can't leave the office until 5pm. (Joanne, I'm for realz so sorry about your luck.)

+ You're so used to working from your bed that your room looks like a frat house. (Empty Cheeto bags on the floor is totes norm, right?!)

+ You wouldn't have it any other way... and just when you think you've reached your limit with all of the plates you're spinning... you find yourself taking a selfie with your boss and hashtagging it #joblove and you know what? You really mean that shit.

You really, really (mostly) do.


If you're an entrepreneur who wants support regarding teams and how to better care for your employees, reach out! If you're an employee who wants to try this whole entrepreneur thing on for yourself... reach out as well. Here at Upspeak we are all about helping you be your best boss self and that includes recognizing where your strengths and opportunities lie. We want to partner with you to grow into that dream job you've always wanted as you learn to better manage your dream team.



Owner | Consultant

The Upspeak Collective |

Meg Witt