6 Things I Learned in My First Two Years of Small Business Ownership

Lessons From Working Hard, Being Ripped Off, and 10Xing my Brand

In September of 2015, I launched Proline Creative, my one-woman content agency. It’s been two years since I took that big leap, and Proline has been cruising along beautifully since then. I’ve grown 10x year-over-year since launching the company, and have had the chance to work with some fantastic brands in dozens of interesting verticals.

Before starting Proline, I had virtually no entrepreneurial experience whatsoever. While I was a well-trained writer, I had never run my own company. Casting off the shackles of desk-jobness and launch a brand was two thing I knew very little about. Fortunately, I’ve learned a thing or two along the way. Here are some of the “Greatest hits” from my first two years of small business ownership.

1. Everything Ebbs and Flows

If you’re going to be self-employed, you’ve got to be profoundly comfortable with uncertainty. Business ebbs and flows. Work comes and goes. Long-term clients shift their visions over time. Employees come in and out.

While you can take proactive measures to offer an attractive workplace, hone your target audience to avoid wasting time on unqualified leads, stash funds for a rainy day, and growth hack your strategy, none of it will help you unless you understand that self-employment can sometimes feel like a standing on a slippery roof with nobody there to break a potential fall — except yourself.

While this uncertainty scares lots of people away from business ownership, it can be a good thing, if you let it. When you know nothing is granted, you work harder to create stability for yourself. In my experience, this creates dynamic, driven professionals who will leap walls and bust through barriers to get to their goals.

2. You WILL be Copied

Around the time I started Proline Creative, I had a very close friend who was considering a career switch. She asked me about writing, and I gladly told her everything I know about making a living in the freelance universe. Not two months later, though, it came to my attention that she had quite literally cloned my company — down to the description (SEO copywriting) and the niche (small businesses and startups) — without my knowledge.

It was a shocking trespass. It remains searing and painful today.

While I had spent six hard, bootstrapped years freelancing, writing for magazines, working with large content agencies and thousands of clients, learning on-page SEO, getting certified in both Content and Inbound marketing, and undergoing professional training for Content Strategy, social media marketing, email marketing, and more, this girl just made the decision one day to brand herself as an SEO copywriter, and out she went.

There are a few things explicitly wrong with this. One is that a move as clueless and opportunistic as that one is bound to destroy a friendship, which it did in our situation. The second is that there’s a significant amount of liability involved with marketing yourself as something you aren’t and never were.

Here’s what I’ve realized, though: at the end of the day, she’s the one who had to rip someone off to build herself an identity, not me. While I took the time to develop a skill, learn a craft, study under experienced professionals, and work my way up in an industry, she just dropped in on coattails and put on a cloak she never earned.

If you’re going to do something original, you can expect to be copied. Breaking trail and walking into the wind both require a strong backbone, honed problem-solving capabilities, and lots of steely commitment. Unfortunately, most people don’t have that quality of character, and the ones who don’t prefer to fall in behind you and ride your wake through the storm. It’s easier for them, and it allows them to pretend they were willing to do the work, in the first place.

Here’s the great news, though: if you’ve put in the effort to create an original game, it means nobody else will be able to play it the way you have. If you’ve taken the time to build skills, gain experience, and bootstrap your way up, you’re already way out ahead of the pack, and your commitment to the game is stronger than anything anyone else can manufacture on a whim.

With that in mind, put your blinders on, put your head down, and get back to work. They’ll fail as copies while you succeed as an original.

3. You’ve got to Keep Leveling Up

At the start of my career, I was working with a large content creation agency. It’s through that organization I got my training as an SEO copywriter, SME, and Content Strategist. During my three years with that agency, I learned a great deal about how to be an effective writer and how to work well with clients.

At some point, though, my personal goals started to outpace what I could do with the agency. So, I left. It was a little scary, and a little uncertain, but it turned out fine, and it’s since made more room in my agency for high-level clients of my own.

If you want to keep growing, you’ve got to keep leveling up. Sometimes, this means leaving the warmth and comfort of a “good enough” situation, but it’s always worth it, in the end.

4. Your Company Needs a Financial Plan

I grew up watching my parents be awful with money. Every major purchase came out of left field — a total surprise and forced them to scrap and save before they could leap. It’s not that they didn’t make enough money, but that they didn’t save, invest, or allocate it intelligently.

I never wanted this for myself, and it’s part of the reason I’ve become so deeply devoted to intelligent financial management, both in my personal and professional life.

Today, I use a strict budget to manage Proline’s monthly spending. I also utilize auto-saving tools, invest, and pay for virtually everything with cash. To prevent your pocketbook from running dry, maintain a financial plan. The more efficiently you can plan things out, the more likely you’ll be to keep trucking along the way you want to, and to avoid the vice grips that commonly affect cash-strapped brands.

5. You Should Always go With Your Gut

Every time…let me repeat…every time I have ignored my gut feeling about something in my business, it has turned on me. The decision to work with that client who seems like a headache, or give that unqualified employee a chance, or take that job that seems disorganized and confusing — all these things turn out to be more trouble than they’re worth.

If you want to run a successful small business, you need to go with your gut. Instead of compromising your ideals, standards, or price, stick to your guns. Not only will you stay truer to your original vision, but you’ll also enjoy a less stressful trajectory to the top.

6. There’s Always a Way to Solve That Problem

As a general rule, people give up too quickly. This goes for relationships, physical exercise, and business. When things get hard, 90% of people tuck tail and run, looking for something that’s more comfortable. Unfortunately, all that leads to is a fractured life in which things seldom get done. As a deeply outcome-driven, Type A person, this tendency drives me insane.

If you want to lead a life that goes even moderately against the grain, or in which you achieve your dreams, you have to keep striving. Yes, life tosses some real doozies at us, but the people who get through them are the ones who put their shoulders against the obstacle and keep pushing until it moves.

One of the biggest lessons I’ve learned through running my own company is that there’s almost always a way to solve that problem. The only thing separating you from the answer is your willingness to get creative and keep moving.

An Ode To The People Who Create Their Own Paths

We live in a time when the opportunities afforded to us are virtually limitless. With dozens of smart, savvy companies vying for talent and the path to self-employment more acceptable and respected than ever, we have the power to produce virtually any result we can imagine.

To the people who use that power to go their own way — I salute you. To give birth to your vision is a trying, difficult process that requires stamina and smarts. While it’s a path that’s not without bumps in the road, it’s one that I believe is well worth the trial and effort it requires.