The Cold, Hard Truth About Being an Entrepreneur Girlboss


When I launched my business at the end of 2015, I had NO IDEA what was in store. There's a million positives along with quite a few negatives of being a business owner. I wanted to expose the not-so-easy realities today in hopes of helping anyone considering entrepreneurship! This is the cold, hard truth about being an entrepreneur girlboss:

  • You feel entirely inadequate when you launch and almost quit many times.

  • You have some (okay, many) 3 a.m. nights and you're so tired that you don't have time to focus on your appearance. Yay for ponytails, buns + non-existent eyebrows!

  • If it wasn't already, coffee quickly becomes your best friend. As does Red Bull.

  • You don't know how to handle difficult clients in the beginning and it will feel super awkward to put your foot down, but you catch on through trial and error.

  • Your clients expect a lot from you - yes, occasionally including items not outlined in your contract, and you naturally learn to bend a little (but not break).

  • Unless you've done this before or get lucky with an accountant friend/relative, you won't understand taxes the first time you file (don't save 15% - save closer to 30%!).

  • Demanding what you're worth feels intimidating, but it must be done in order to keep your head above water (ex: charging higher rates to cover your insurance and taxes).

  • A lot of people, including those not operating their own businesses love to condescendingly tell you how to act and what to say, and 8 times out of 10 they are wrong or are simply telling you something you already knew. This especially happens when you're young and female. You learn to take it all with a grain of salt.

  • Your website and social media are your strongest first impression besides your business cards. All these items are an investment that you have to account for as well, but the good news is: you can write the $$ off at the end of the year!

  • In a single moment, you've become not only CEO, but the accountant/bookkeeper, the janitor, the PR/marketing person and the assistant that answers all emails.

  • You often find yourself frantically typing away while you + your sweetie are trying to enjoy a nice dinner while watching television and you force yourself to take breaks.

  • Planning a vacation revolves around your WiFi connection at the hotel because you cannot be away from the Internet for even two days and expect to run your business smoothly without something catching on fire.

  • You order a LOT of takeout because it's convenient and you're exhausted. Cooking a nice, healthy meal for dinner pretty much guarantees that you're not getting any client work done that evening - and don't even get me started on doing the dishes!

  • Social events often take a backseat and you're at home many, many Friday nights.

  • #TGIF is not in your vocabulary unless you're drafting social media posts for clients. Your Saturday is as crucial as your Monday and you often work weekends.

  • Because you're operating your own machine, your budgeting skills become much stronger, but you almost compulsively track your income. It can get annoying.

  • You practice your 10, 30 and 60 second elevator pitches in hopes to nail them down before you meet your next prospect. These start off painfully uncomfortable, and you never truly feel confident pitching yourself and your talent, but it must be done.

  • Not all of your friends and family support you, or even care to know what you do, even if you've supported their entrepreneurial efforts. I've been asked by people I consider dear friends, "So, you've done before?" when is literally what I do to make my living every day. Not every Facebook friend likes your new business page or actively cheers you on - you are your #1 cheerleader.

  • Your motivation and success solely rests on your own shoulders. I was lucky enough to grow up in alternative, self-led education where I designed my own high school and college curriculum and chose whether I failed or succeeded, but if you aren't used to this concept of self-driven action and motivation, it's quite challenging.

  • People who crave the inside secrets of your profession solicit free advice and consultation from you because they just so happen to notice that you launched a business (just take one look inside my Facebook Messenger!), sometimes without even offering to buy you a coffee or lunch, let alone asking for your rates.

All in all, launching a business is a thrilling and unique experience that not every individual gets to have in their lifetime. Believe me when I say that it is so worth it. If you're up for the challenge, I suggest taking the leap of faith and defying your deepest fears of failure and inadequacy. You wouldn't want to go another day without knowing your potential, right?

Are you thinking of launching your own business? Already have one?
I'd love to hear about your experiences!




Kathryn is the lead contributor + founder at Obsessed with leading a life of balance, she started the blog in 2013. Since graduating from The Evergreen State College (Washington) in 2016, she is now a digital marketing specialist through her business, Fashionably Frank Marketing. She believes a cup of coffee is the answer to all of life's problems + that all women should strive to embrace a #girlboss mantra.