What the first year of business is really like - #nofilter

Author: Ashley Adair, Founder & CEO Blue Shoes Leadership, LLC

Right before my last day at my corporate job I found myself trying to Google what to expect in the first year of business. Most articles talked revenue and stats, but I wanted to know more about the day in the life.


So, before I start to romanticize and misremember the first year, I figured I owed the internet another perspective. Here’s what it’s really like, for all the new entrepreneurs out there. #nofilter



Day four will smack you into reality.

The first day being 100% employed by your business feels like Christmas morning. If this was a movie montage, Michael Buble’s version of “Feelin’ Good” would start right as your feet hit the floor.


Before I got to this day, I’d interviewed every entrepreneur I knew to get the scoop. What would the first full-time day feel like? I naively thought if I knew common pitfalls I’d be able to glide past them. Because, ya know, I was gonna be different (Eye.Roll.). One business owner warned me that I’d feel a lot of emotions the first week. She warned that they’d come on from nowhere and that she was a mess the first day. Well, at the end of day one I hadn’t cried. Smugly, I patted myself on the back. Clearly, I was already killing it.


It wasn’t day one or day two. Not day three. At this point I assumed I had beaten the system with my exceptional-ness.


No, my friends, it was day four.


On day four I’d found myself at what we call the entrepreneur ‘trough of despair’, and girl, everyone will eventually drink from it.


Every problem was big, and unsolvable. Every idea – absolute crap. Then I did the worst thing ever – I checked my Quickbooks. Hot tip: don’t do that on the fourth day of full-time entrepreneurship. Its about as useful as reading the comments of anything.


Pause. Truth time. As I share this now, I find myself wanting to edit out the imperfections. Rub glitter on it or apply a flattering filter. It would be easier to tell you that it all “totally, definitely works out and I couldn’t be happier!”. But I just watched Brene Brown’s Netflix special, so I won’t do that.


The first year is kinda like glitter, now that I think about it. Sometimes it’s fun and pretty, and other times it’s on EVERYTHING and won’t. come. off. And sometimes you end up crying in the bathtub on a Tuesday night over everything and nothing. Day four happens, (literally and metaphorically), but crying in the bathtub has nothing to do with what the future holds for you. I've learned you can’t just get through a ‘day four’ type of day, you have to feel your way through it.



photo by Sharon McCutcheon via Unsplash



Fear becomes your roommate

You may not have known it, but when you decided to take the leap, you also gave the keys to your new roommate. Get ready for Fear to just move right on in. Fear is the shittiest roommate by the way. Shows up to give you “feedback” on things you feel good about (and especially on things you feel self-conscious about). Invites their friends Shame and Guilt over way too much, and those assholes ask you how your business is going all the time!


But then one day, they start growing on you. You’ll realize they are good at identifying great ideas. They just tell you not to do them, and those are the ones you start putting all your energy into. You begin to get comfortable having them around. And then a magical day will happen, when you’ll walk in the door and they’ll all be playing Mario Party on your couch and instead of freezing up, you say “oh hey, what’s up”, grab your La Croix and go to your room to tackle your next whatever.



All your ish floats to the top

Great news! Do you have some unresolved confidence, self-image, or worthiness issues? You’ll be dealing with all those things and more exactly… RIGHT NOW. Because all your shit is about to come out. Save yourself some time and just order all the Brene Brown books, pre-schedule therapy for a year, hire a business coach, and join a wine club. I’m being serious. As much fun as seeing the results of a year of growth is, it doesn’t feel so great every moment.


The Oxford dictionary’s definition of growth is “The process of increasing in size”. It might be invisible, but you are in the process of increasing yourself. There is only one time we as humans expect people to focus on nothing but increasing in size. And it’s when we are infants. They do nothing, we expect them only to grow, develop, and get stronger. So, not only are you doing that, but you are trying to run a business, get enough sleep, water, and exercise, stay showered, wear clean clothes, go to networking events, go to the thing, be the person, have the idea…I’m tired just writing that.


Oh? And baby-preneur, if you were thinking of going to B-school at the same exact time as all this – while it’s possible, I can’t say I’d give it exactly 5 stars - you feel me?


So, with all that, is it surprising that your ish floats to the top? For the first time in a long time you will be so raw and tired that the masks fall away and it’s like breathing in ocean air with your eyes closed and when you open them, you hear yourself say “Here I am. Finally.”


And it feels really fucking great.


Enthusiasm doesn’t equal invoice paid.

Oh, this one is short I promise. I really wish I would have known that excitement and coffee dates and enthusiasm doesn’t equal bookings. Or that bookings don’t always equal payment. And some friends may just root for you, but other friends will get in the arena with you -- and both are okay.



RSVP for yourself

“Sometimes the bravest and most important thing you can do is just show up”. My girl Brene said that and it’s written on my white board as I type this. It couldn’t be more of a cliché and yet, couldn’t be truer.


Some days you’ll stay in bed. Some days you’ll jump out of it. And some mornings will drag until you’ve had your morning cup of productivity juice. And once you move from knowing your business was a good idea to believing in it – that’s when you’ll be able to say you are a founder without it sounding like a question. That’s when spell check will stop reminding you how to spell entrepreneur (okay, I still struggle with that one).


And if you need to hear it, even if it’s just from the voice inside your head reading this: I believe in you and your business. You are capable and worthy of doing this. You have everything you need to succeed. You made a great choice. You got this. Everything’s okay. You’re a badass.


P.s – Make entrepreneur friends ASAP and schedule time to hang with them. Ideally on your "day four".

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