15 Lessons from Year One of Having My Own Business

15 Lessons from Year One of Having My Own Business

How to not go broke OR insane.

I’ve never thought of myself as much of an entrepreneur. I didn’t run a lemonade stand as a kid; networking events are my personal hell; and I hope I never own a skirt suit. I’ve never even taken a business class before.

And yet, armed with more book smarts than street smarts and a business repertoire almost solely gleaned from my entrepreneurial parents and the StartUp podcast, my boyfriend and I started a little video production and copywriting company. And over the past year, that little company got an office, and contractors, and clients.

Thesis: If I can do it, you can too. While I’m still far from an expert, here are a few lessons I learned in Year One.


1. Work smarter, not harder.

The bags under your eyes and your “I AM SO BUSY” phone case aren’t measures of success. Saying no to projects and clients that don’t align with your vision or values can be one of the hardest things when you’re just starting out—especially when they’re dangling dollars in front of you like dog treats. But if your calendar is full and you’re barely breaking even, or if you’re flush financially but aren’t doing the types of jobs you set out to do, that’s working hard—not working smart.


2. Know your numbers inside and out.

And backwards and upside down. (Programs like FreshBooks and YNAB are awesome tools for understanding your cash flow and managing a budget if you aren’t a natural at accounting.)


3. Get a line of credit.

Right away. And use it. Having that cushion in case checks come late (because they do) or your Mac breaks down (because it will) or your house catches fire (true story) will keep you sane on this roller-coaster ride—and it’ll help you build credit if you consistently pay it off.


4. Prioritize your health.

Admittedly, I’m hungover and subsisting on a diet of 80 percent known carcinogens as I write this. But staying healthy, both physically and mentally, is imperative in your first year. Who’s going to finish that project on deadline if you’re out of commission for a week?


5. Fuck the 9-to-5.

You make your own rules now. If you work best from noon to midnight, do it. If you work better on weekends than weekdays, do it. Test-drive different routines until you find the hours that work best for you.


6. Set up an Asana or Basecamp account.

Your bullet journal is all well and good for color-coding your grocery list, but you need an easy, automated way to stay organized, manage projects, and stay on top of everything.


7. Look into a co-working space.

Entrepreneurship can be a lonely endeavour if you’re working out of your kitchen. Being surrounded by other people isn’t just energizing—it helps you meet potential clients and collaborators in a non-network-y way. And if you’re like me and miss your old close-knit office environment, it’s a great way to stay social.


8. Stay inspired.

It’s easy to let reading your bi-weekly New York Magazine or seeing Moonlight slide to the bottom of your to-do list when you’re on the grind—but it’s impossible to stay relevant when you’re living under a rock. Consciously carve out time to read new books, watch new shows, and try out that new restaurant with the disco lights in the bathrooms (shout out to Otto’s Bierhalle—thanks for the inspo and the schnitzels).


9. Make traditions early.

Whether you’re starting on your own, or with a small team, youre laying the groundwork for a company culture right from the get-go. So kick off those Mimosa Mondays or Fenty Slide Fridays already.


10. Under-promise, and over-deliver.

I can’t count the number of times I’ve stayed up till ungodly hours because I over-promised on deliverables or agreed to an unreasonable deadline. Being up-front about your capabilities and time lines can save you a boatload of unnecessary stress—youd be shocked at how many clients are perfectly fine with waiting an extra day or week, saving you from Kim K-crying at 3 AM into a bucket of ramen.


11. Try not to gossip about your company.

Who doesn’t love to complain about their job, right? But when you’re in the early stages of shaping your brand, every eye roll about a crappy client or sarcastic remark about an employee is contributing to your business’s reputation. Perception is reality—the more people viewing your company as happy, healthy, and all-around awesome, the better.


12. Get a mentor.

Or a partner. Or someone you can run ideas by who won’t just pat you on the head and tell you you deserve all the Oscars (hey, Mom!). Establish your go-to crew early on, and make sure they complement your weak spots (i.e., if you’re a creative with terrible spelling, there should be a natural copy editor on your makeshift advisory board).


13. Organize your thoughtfulness.

When we were in startup mode, I was Dory from Finding Nemo when it came to remembering best friends’ birthdays or checking in on my grandparents. Put “BUY BIRTHDAY CARD BY” dates in your calendar. Make recurring tasks on your to-do list to call your dad. Whatever you have to do to make sure your personal life doesn’t fall prey to your professional life.


14. Remember why you’re here.

Remember all the times past bosses, professors, and friends told you that you were destined for big things. When the impostor syndrome starts to sneak in—and it will—remember who got you to where you are: you.


15. Celebrate!

You’re doing something really hard and stressful, and you’re going to have your fair share of funeral home-y vibes floating around. So celebrate all the little things that turn a regular day into a good day. Nice email from a client? Make sure everyone who worked on the project feels the love. Two checks come in the mail on one day? Pop that bubbly. Still going strong at the end of Year One? Hug it out, cause that shit ain’t easy.

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