Six Lessons in Six Months: What Starting My Own Business Has Taught Me (So Far!)

By Ellen Lichtenstein, MA
Owner, Just Add Communications LLC 

Being a business owner is, apparently, in my blood. 

My father, mother, grandfather, aunt, and three different uncles are just the first business-owning relatives who come to mind. In fact, my great-grandfather, a Russian immigrant, started peddling goods out of a wagon until he was successful enough to open a shop. His entrepreneurship must have trickled down by nature, nurture, or both. 

While some people might see starting a business as a major undertaking—and, don’t get me wrong, it is!—I have spent my life surrounded by people who did it, and succeeded. This might have led to a false sense of confidence when it came to starting my own company. Or, it might have made me more realistic about the challenges and rewards of being self-employed. After all, I spent my adolescence with my stepdad married to his cordless phone, invisibly tethered to a 100-foot radius around his home office, lest he miss an incoming call from a customer. This was before cell phones were widely available. 

When I began to contemplate going into business for myself early in 2020, the idea only appealed to me on an emotional level. I reveled in the thrill of independence: the freedom to do what I wanted, when I wanted, and how I wanted. On the rational side, it scared me to death and didn’t sound like a good idea. AT ALL. 

It was only after realizing I couldn’t continue in my current full-time role and maintain any sense of mental and physical wellness; only after I was rejected by several promising companies with lengthy interview processes; only when I realized that no “boss” would ever value my work the way I did, that the “choice” to start my own company became a calling. 

I use the word “calling” very intentionally. As anyone who’s ever done it will tell you, starting a company is hard work. Long hours and hustling for every client, all so you can spend a year (or more) being unprofitable: this is what you’re told to expect. I don’t know anyone who would choose that if they didn’t feel called to it. This deep sense of knowing with certainty that I am exactly where I’m supposed to be is one thing that keeps me going when the frustrations pile up. 

It’s now been six months since I took the plunge. I have no regrets, but I’ve come to a few realizations along the way. No doubt, the lessons will keep coming on a regular basis! I am by no means old, wise, or seasoned in this business stuff. But, in the spirit of giving (it is Christmas, after all!), I am sharing the six biggest lessons I’ve learned in my first six months. 

One: There's probably never a "good time" to do something risky
 
It was June 2020: I saw talented friends and colleagues being laid off and struggling to find work. Leaving a job intentionally did not seem like the smartest idea. A good salary, benefits, a secure position that could easily be done remotely: why would anyone walk away from that in middle of a pandemic? 
 
I also realized, much like other things in life, there’s never a “good time” to take a major risk. How many times do we put things off, waiting for the exact right moment, only to never actually do them? 
 
Like the diet we’ll start after the next holiday, or the vacation we’ll take when we have the free time. It dawned on me how true the saying is: The best time to start something was yesterday. The next-best time is now. 
 
Two: If people believed in me, it was for good reason
 
Who among us doesn’t suffer from at least the occasional bought of imposter syndrome? When I first started floating the idea of going into business for myself, I was shocked (SHOCKED, I tell you!) by the responses. 
 
“Oh, that’s wonderful! You are going to be amazing!” 
 
“This is perfect for you. You’re going to love it!” 
 
Not a single person said any of the things I was thinking. No one questioned if I was good enough at my work, if I was organized enough, disciplined enough, or whether I had fully thought it through. 
 
Though I had my doubts at first, I figured everyone I knew couldn’t be so wildly wrong. Turns out, they were absolutely right. 
 
Three: Self-promotion isn’t selfish 
 
I had this nightmare. I would build an amazing website and announce to everyone in my network that I’m self-employed and open for business. And then, crickets. I dreaded the thought of having to bug people and remind them I’m available for work. I feared coming across as self-serving if I mentioned my business in casual conversation. 
 
Turns out, I was entirely wrong. No sooner had I updated my LinkedIn, than I started to get messages from friends, former colleagues, and even businesses I’d patronized in the past. They needed websites designed, blogs written, and communication strategies formed. I cannot tell you how many times I reached out to someone just to let them know I have a business in case they ever needed anything, only to have their first response be, “It’s so good to hear from you! I am in desperate need of your services!” 
 
I realized my potential clients need me as much as I need them, and it does neither of us any good for me to be shy about what I’m up to. 
 
Four: If you love what you do, you’ll never work a day in your life 
 
As cliché as it sounds, I have to admit it’s a little bit true. Now, there are parts of running my own business that I absolutely hate. Like the time I had to “fire” a client, or when I have to remind someone to pay an invoice more than once or twice. 
 
But, when I’m doing the parts I love? Absolutely! I’ll spend five hours designing a pitch deck for a TV network without coming up for air. I get engrossed in my writing, video editing, or any other creative pursuit, and I’m lost to world.
 
What would you do if you didn’t need to earn a living? My answer is, pretty much, exactly what I do now. That’s how I know I’m on the right track. 
 
Five: Say ‘yes’ and figure it out later 
 
The first three clients I had were in need of a website. I am NOT a web designer. I was, however, in need of clients. This lesson actually isn’t a new one for me: I’ve made a career out of agreeing to do things I’ve never done before and then learning how to do them along the way. 
 
I know my limits. It’s not like I would agree to fly an airplane! But, within the confines of reality, I am a huge proponent of faking it until you make it. It’s been an incredible challenge—and blessing—to take on jobs I wasn’t really sure how to do. As they say, that’s where the magic happens. 

Six: Sometimes, I really need to take my own advice 

The premise of my business is simple: Let me handle your communications so you can focus on what you’re best at. At the same time, I spent my first few months trying to also be my own accountant. Because that’s definitely my area of expertise and the best use of my time, right? 

Let’s just say, not so much. 

As lesson number five indicates, my instinct is to assume I can do everything, even if I don’t know how. While this has served me well within my field of expertise, the same cannot be said for all the times I’ve tried to be my own accountant, lawyer, or dentist. It’s like I’m always telling people: some things are best left to the professionals! 

Taking my own advice and handing things over to the experts has been difficult. It costs money (and, if there’s one thing a new small business doesn’t have…) but I’ve realized outsourcing these things is a necessity. I’ve also learned that it costs more in the long run to try to cut corners, and costs, at the start. 

As I reflect back on my first six months in business, it feels surreal. It’s scary, exciting, and liberating. Most of all, though, it’s empowering. 

In fifteen years of professional work prior to this, I often felt unsatisfied. Regardless of the industry, company, or job title, it never felt right. 

I wanted to do things I love and am good at, not be assigned menial tasks that bored me. I craved to be recognized for my individuality, not told to conform. I wished for the freedom to innovate instead of being told to follow procedures. Not least of all, I wanted to get paid what I was worth, rather than seeing others profit off my work and barely getting a fraction of the value I provided. 

Starting my own business, as terrifying as it was (and still is), has solved these problems. Of all the lessons I learned in the first six months, this one may actually be the most important. 

Seven: There was never anything wrong with me. I was always good enough. I just wasn’t in the right place, or with the right people, to realize it. Until now. 

About the writer, Ellen Lichtenstein

Ellen Lichtenstein (pronouns: she or they) is the Owner and Founder of Just Add Communications LLC, where she specializes in providing marketing, communication, and content creation services to businesses of all sizes. Her diverse range of clients spans from independent insurance agencies to media companies to large software and technology firms, and beyond. 

Prior to starting Just Add Communications, Ellen spent eight years producing and casting documentary and non-fiction television, followed by seven years working in content and communications within the insurance industry. 

Originally from Birmingham, Alabama, Ellen has lived and worked up and down the East Coast, throughout the Midwest, and now calls Denver, Colorado home. She received her B.S. in Communication Studies from New York University and her M.A. in Communications from Johns Hopkins University. 

Outside of her primary business, Ellen is passionate about horses and volunteers with The Right Step, Inc. therapeutic riding center. She is currently launching her second business, Leg Up Learning Solutions LLC, which provides both riding instruction and Equine Facilitated Learning to help individuals and groups become better listeners, leaders, and communicators through working with horses. 
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