Entrepreneurship | What They Don’t Tell You

C/O Rent the Runway

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.

hot pink jumpsuit


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.



hot pink jumpsuit



hot pink jumpsuit


Photos via Style Charade


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  • Appreciate your candor and authenticity, Arin. Many women wouldn’t open up like this, and it’s so refreshing to watch you take control of your life and brand – as hard as it is sometimes. I’ve got your back girl!

  • I LOVE this post and how much insight you wrote in it! I started by blog about 7 months ago and thought getting readers and affiliate programs would be super fast. Totally not the case. There are days when I only get spam as blog comments. Then there are the days when no one comments on the blog and I’m like wait, my material is so bad that spam won’t even comment?! I can relate to a lot of these gorgeous, but just know that your blog is beautiful and the material you post is great! I hope you’re having a day as wonderful as you are!

    xx Julianna
    IG @julianna_claire

  • You talked about comparing success…this is a trap I have found myself in countless times. I had to redefine “success”. Success looks different for me than the people I was comparing myself to which just tore me down. I had to start thinking about what success means to me. It’s a challenge but one that changed the comparison game for me. Next time you’re tempted to compare your success, figure out what success looks like for you. It’ll be different than the person/thing you were comapring. ?

  • Once again a fabulous post! I love reading these types of advice posts and they really resonate with me. I envy the fact that you were able to build up the courage to leave your full time job and throw yourself into your freelance/blog career. It’s something I think I’d like to eventually do down the line, work for myself, and it’s incredibly interesting and helpful to read about it from your point of view! Thank you 🙂