Entrepreneurship | What They Don’t Tell You

I recently attended the Create & Cultivate conference in Chicago (Thanks for the ticket, Whitney Port!) & it was full of entrepreneurs, girl bosses and wisdom. As many of you know, I left my corporate job to pursue my passions (and blog) about 6 months ago. I can’t even begin to describe the feeling of walking into my boss’s office, and giving notice; I was elated. You can read more about my journey here, but it certainly was long overdue. I think we all reach a breaking point in our lives; for me — it was time. I decided to put my happy above a paycheck. (Easier said than done, of course). Slowly, as I begun this journey of self-employment, freelance, and entrepreneurship, I realized something: The media glamorizes working for yourself. (One of my favorite takeaways from the Create and Cultivate conference). Don’t get me wrong, I absolutely love this path, and will continue to follow happy (wherever that may be). But, there are a few things I wish someone would have told me before taking the leap.

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Money: Unless you have a Daddy Warbucks in your life — you’ll be scraping by. Personally, I live with my boyfriend, and he’s my biggest supporter (I am always upfront with people about this aspect — although: I would have left my corporate job either way. When you’re miserable, you find a way to make it work). Every decision you make is through a financial lens. I think this is one of the toughest aspects of starting a new journey — you have a lot of limitations. People start doubting you, and you have to say no to a lot of fun things. Going out with girlfriends is pretty much a thing of the past, and I can barely afford a tee from Forever 21 (seriously though). I feel like I’m back in college living paycheck-paycheck — It’s a tough adjustment going from a salary/benefits to counting every single penny. Again: I would rather be broke than miserable, but it’s still really tough some days. As miserable as I was in corporate, sometimes — I actually think that life was easier. I mean, I had HR taking care of all my financials, and benefits. Long story short: I thought the money would come a lot easier. 

Healthcare: Nobody prepares you for the hell of healthcare. Honestly, I still have no clue what I’m doing, or what I’m paying for. I do know that I pay a lot out of pocket (like, my entire paycheck) for little coverage. The system is a total rip-off, and I wish someone could have showed me the ropes of signing up, and making the right choice. Anyway — I think I’m finally understanding this world, so if you need some guidance: holla at yo girl. PS: I’m sorry to the Blue Cross Blue Shield folks for crying over the phone. It’s an emotional time!

Lonely: Working for yourself is lonely. No more coffee runs with my colleagues, or gossip-hour near the water cooler. I am spending the majority of my time staring into a computer screen at home — alone (In my PJ’s with Saved by the Bell) Oh wait — that actually sounds really amazing. In all honesty: Sometimes, I miss having someone to talk to, or actually understand what I’m going through. Also: I wish I had more support. You have a lot of doubters, and competition.

Doubt: There are some really shitty days in there — like, really shitty. (I know we can all relate to this: self employment, or corporate) but, when all is riding on ME; kind of changes things up a little. Your business will challenge you, and you’ll lose faith in yourself. I can’t lie: There are so many days where I’ve looked for a job (even interviewed) because I didn’t believe in myself. This journey is a roller coaster ride, and it’s important to realize you’re going to face some serious forks in the road. This is all part of the plan — the grand picture. Truthfully, I’ve learned to keep frustrations to myself — I’ve realized when I voice my concern (especially financials) to the people I care about, they’re the first people to tell me to go back to work. I need to push through the frustration — if it was easy, everyone would be doing it.

Don’t Compare: Ugh, the evil comparison game. It’s natural to compare yourself to success — but, don’t let it get you down. Too many days have been spent with comparison, tears and doubt. I’m still learning to overcome this, but I notice a positive difference in each day.  (Check-out my post on Glitter Guide for more on this topic!) 

24 Hours: Yup, no such thing as a 9-5 anymore — When I left my full-time job, I was most excited for the flexibility (which rocks). I didn’t realize that I would actually be working more hours — But, doing what I love is a huge game-changer.

No: Learn to love this word, because regardless of what’s on your resume — some people don’t give a shit. For every no, there’s a yes somewhere. Don’t give up, keep your head up! Someone will believe in you. (It just takes time!)

Overnight Success: You’ll need to learn patience, and a lot of it. It’s really hard to find freelance work, and paid opportunities. Initially, I thought this was something I could do in a matter of weeks, but turns out: It’s taking a lot longer than that. Things never go as planned, and you should always have a back-up plan. For me, it’s working part-time to meet the bills. One day — I’ll be able to transition entirely — but, it takes time! 

It’s not as cool as it looks: From the outside, it looks really cool. (And some days, it is!) But most days are a struggle. A struggle to find work, and keep focus. A few things I’ve realized thus far: Discipline, confidence and strength go a long way. You have to believe in yourself first, or nobody else will. Believe, and you will receive.

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Photos via Style Charade