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Honest & Genuine Advice for Launching your First Business

office attire

Five years ago, I launched my very own freelance design business—Leap. It became my full-time job upon moving to Chicago and over the years grew into a burgeoning and successful design company. I’ll be honest, when I first started, I didn’t have any idea what I was doing or any real plan for the future. My main concern was securing enough projects each month to cover my rent, bills, groceries and kibbles for Oliver.

As different road blocks came up, I dealt with them as best as I could, but I never felt prepared for the different problems and milestones I ran into along the way. Sometimes my fly-by-the-seat-of-my-pants strategy worked fine and other times it backfired and I found myself in shambles, crying at my desk, not knowing what to do.

Since the initial launch of my design business, a lot has changed. I’m no longer designing blogs, and this blog has become the biggest part of my day-to-day job. While it doesn’t always feel like a job, which I feel incredibly lucky for, at the end of the day, it is a business, and I treat it like one.

military blazer

scalloped cami

I learned a lot from my blog designing days and those lessons have made the transition to my new job so much easier, so today I wanted to share a few pieces of advice that I’ve learned and wished I’d known when I first started.

1. Keep Track

Whether it’s a spreadsheet or Quickbooks, make sure you keep track of all your invoices—paid and unpaid—and your business expenses. It makes tax time easier and keeps you from forgetting to collect payment on projects (I’m guilty of doing this in the past). I also like to keep track of my growth. I have a separate spread sheet for traffic and social followings. Sometimes you forget where you started, so having this on hand is a good reminder to see what you have accomplished or just the thing to fire you up to work harder!

2. Do it Your Way

There’s no exact formula for running a successful business. So find what works for you and own it. Just because you don’t start working at 9am like the rest of the world doesn’t mean you’re doing it wrong.

3. Dress the Part

For me, getting dressed for my job is the one thing that gets me more motivated and makes me feel more professional than anything else. More than anything, it’s a confidence builder! If you look good, then you feel good, and this outfit is a total girl boss look if you ask me. My very first job was very much business professional—I wish I had known about these pants then. I love they way they fit and the ankle length is so cute!

Now that I work from home, I like putting my own twist on business casual. For this look, I paired an ultra feminine top with a structured jacket and ankle pants—I love this combo. Lately, I’ve been loving Express’ Wear to Work Collection because it has the basics, but also has so many pieces that are totally appropriate for the office, but infuse a little more personality. I love this simple scalloped cami—it’s reversible too!

scalloped cami
what to wear to work

work outfit

4. You Don’t Have to Invest a Lot

Depending on your business, you might have more upfront costs, but for me, I started with nearly nothing. All I paid for were my design programs, which Adobe’s Creative Cloud now makes even more affordable, and dirt cheap hosting for my website. If you need a professional website, but don’t want to spend a lot, there are so many cheap options for amazing looking sites these days!

5. Know When It’s Time to Hire Help

Just because you’re starting your own business doesn’t mean you have to know everything. If you need a website, but don’t have a background in it, hire someone to make it look professional. Accounting? No, thank you. Hiring an accountant last year was one of the best decisions I ever made. I’m less stressed come tax time and don’t worry about forgetting important payments anymore.

There comes a point when you realize you can’t do everything, well maybe you can, but you can’t do everything well. Hiring an accountant was easy, but someone to help wit the day-to-day workings on my blog was scary! But, it’s been one of the very best decisions I’ve made. I was able to pass off the work that I wasn’t that great at and didn’t really enjoy, and in return, it’s given me more free time to be creative and focus on the parts of my business that I love. It’s also a huge weight off my shoulders! Just make sure you find someone who’s passionate and reliable!

6. Loosen the Reigns

This one sort of goes with the one above. Giving up parts of my business were scary and I wasn’t sure if someone else would measure up to the level of quality I expect from myself. I also worried about working with someone since I’ve been working solo for so many years. The reality? If you find good people, they do good work!

how to dress for work
what to wear to work

blazer and cami

how to wear a blazer

7. Be Yourself

Probably the best part of owning your business is that you get to create your own work place culture. For me, that means creative, relaxed, but stylish. I’ve designed my workspace to reflect that, and also dress that way on a regular basis to feel most inspired.

8. Have a Support Team

My blogger friends are my biggest support group. We share tips and tricks and genuinely want to see each other succeed. We all have very different audiences, so it takes any competition out of the equation. Other than that, Rob is always so supportive. He’s a great person for me to bounce ideas off of and I always appreciate his input since he works in such a different field.

blogger style
tailored street style

chicago style blogger

9. Have a Plan (And Know it’s Okay if it Changes)

Going in with a plan is smart. It’ll keep you on track and hitting your goals, but if things change along the way, it’s okay to change your plan. Honestly, I thought I’d be designing blogs forever, but last year, my personal interests and goals took a turn and rather than fighting against it, I just decided to let it happen. Guess what? Best thing ever!

10. Remember Your Why

At the end of the day, don’t forget why you started your business. For me, I wanted freedom over my schedule, my income and my hours and owning my own business has given me all of that. On hard days when everything seems like it’s falling apart, I always go back to the why and remember how lucky I am to do what I do.

Have you started your own business? What advice would you give?

BTW, date night at the Art Institute, and how to create an inspiring workspace.

Thanks to Express for sponsoring this post.