I’m celebrating a very special milestone this week: I’ve been self-employed for five fantastic years. Although my company, lowercase d, legally came into existence on June 12, 2013 (incidentally also my birthday, which I took as a good omen), I typically mark mid-July as the official moment when my business began in earnest because that is when I started working on my first project as an independent contractor.
To celebrate five years of a very rewarding tenure as the boss of my own company, I’m taking the day off to party on Friday. I believe it’s important to pause and enjoy your successes even as you push forward to achieve new heights. But hitting the five year mark also offers me a great opportunity to reflect on what I’ve learned so far in the hope that it might be of value to others who are just beginning their own businesses or who hope to do so in the future. With that in mind, here are five things I’ve learned in the five years I’ve been self-employed.
1. You can do it
Starting a business from scratch is terrifying. If you’re not independently wealthy or sitting on some cool VC cash, striking out on your own is a huge personal risk. If you’ve ever struggled with impostor syndrome, well, that little voice in your head telling you you’re not talented or qualified enough is probably fuming with indignation that you would have the audacity to even contemplate such a thing. But that little voice, ironically, doesn’t know what it’s talking about. You can do it.
I learned more about myself by starting a business than I ever could have expected. I always knew writing was my greatest talent, but I never knew that I have a head for business as well until I took the leap of starting one. In my prior job at a toxic workplace, I had been encouraged to believe that I was too risk-averse and too timid, qualities I now know are stereotypically attributed to women. I didn’t actually believe I was like that, but I didn’t yet see the abundant evidence that would make me think otherwise. Then I went into business for myself and took the greatest risk of my life. It turned out to be the best decision I ever made.
The startup period for founding your own company is unlike any other, I’ve come to understand. There are a lot of practicalities to concern yourself with, such as filing the right paperwork, deciding what you want to specialize in, and defining your brand. Sometimes it feels as if there’s no solid ground beneath your feet; other times it’s exhilarating and exciting. But it’s all doable if you put in the hard work, embrace a growth mindset, and tap the resources you need when you need them. As I write this, I’m watching a dear friend start her own business and I’m getting a vicarious thrill watching her plant the seeds of her future success. It’s like nothing else.
2. Your experience is valuable
When I went into business for myself, I also initiated a career change. I departed a twelve year career as a nonprofit IT Director, opting instead to become first a social media consultant, then a social media consultant who was also doing some writing about tech, and finally a full-time writer specializing in tech. It was a gradual transition as I became increasingly comfortable first with being self-employed and then with setting a clear direction for my company.
At the time, I wasn’t sure I was bringing anything of value with me from my old career into the new one. But I soon realized I was tapping a deep well of experience that was very relevant to my chosen profession as a writer. Having been an IT Director at a fast-paced and rapidly growing organization, I am intimately familiar with the pain points that the audience for my articles—mainly IT professionals and business leaders—grapples with every day at the office. I can speak to them in their language and directly address their concerns since they are fellow members of the geek tribe, as it were.
What’s more, I still carry with me the same passion for technology that I had when I worked with it every day. It’s fun to research and write about the latest tech trends and experiences that shape our lives, and that joy comes through in my writing. So although I’m no longer the stoic IT pro toiling away in a server room or the java-fueled IT Director analyzing budgets and contracts while staring down a relentless schedule of back-to-back soul-crushing meetings, those experiences directly inform the work I do now.
In fact, some of the least sexy responsibilities I once held—those pesky budgets and contracts, for example—prepared me surprisingly well for starting my own business. And since I’m a process nerd, I actually enjoy pursuing administrative projects that others might find hopelessly boring, like creating an offline archive of your writing portfolio. This way, I can enjoy the best of both worlds: the sheer pleasure of writing for its own sake and the practical benefit of left-brain business expertise.
3. Your authenticity is an asset
If you’ve worked in a corporate environment or survived a toxic workplace, then you may have felt the pressure to hide your true self at work. That may be the wisest course of action depending on the situation (hopefully not yours), as office politics is a blood sport at many companies. As I learned, though, the reverse is true when you become self-employed. You are literally selling yourself and the value that only you can offer the world. Therefore, you’re incentivized to be as authentic as possible, getting real with yourself about what matters most to you and leaning into your true identity.
I’m a huge Star Trek fan, for example, so I get a total kick out of bringing that knowledge and enthusiasm into my writing about the tech inventions that sci-fi got right. Having grown up in a heavily literary environment (that’s no joke—the Pioneer Valley of Western Massachusetts is uniquely book-crazy, as the New York Times reports), I can infuse my work with my literary sensibilities when appropriate. As a devoted follower of the Boston Red Sox, I’ll bring that genuine voice to any article focusing on sports in general, but especially the one true pastime: baseball. And as a committed progressive and Oberlin alumna, I’ll have something to say when it comes to social justice issues like the state of women in tech.
Since I’ve become a writer, I now know that I turn out my best work in a quiet, solitary environment and I’m not one bit ashamed (nor need I be, since I’m self-employed) about creating a work environment that supports that essential requirement. It’s not a fluffy nice-to-have—it’s what delivers optimal business results. By embracing my authentic self, I’ve found rewarding, stimulating work that aligns with all of these aspects of who I am. As a result, my work life now is far better suited to my personal life—and vice versa. They inform and sustain one another rather than existing in opposition to one another.
4. Business partnerships are essential
I’m an introvert, so in-person networking events involving large groups of people tend to quickly drain my battery. That being said, when I was making the transition from being a nonprofit technologist to being a self-employed social media consultant and writer (and later just a writer), I knew that I needed to build out a brand new professional network to match. As luck would have it, I made a terrific connection at one of those early networking events that I still cherish today.
While I was getting my bearings amidst a deafeningly loud crowd of creatives at a local BBQ restaurant five years ago, a woman came right up to me, introduced herself to me, gave me her card, and said we should get coffee sometime. As I soon learned, she’s an SEO expert who makes a mean cocktail, shares my progressive politics, has a deadly sense of humor, and is a loyal friend. As I was getting started with social media consulting, we partnered up on several online marketing projects requiring both SEO and social media expertise. I discovered the value of having an SEO expert I could refer my clients to, someone I trusted and who I knew, from firsthand experience, consistently turned out high quality work.
Even though I’ve since transitioned to writing full-time, she and I still regularly grab drinks in the neighborhood and compare notes on how business is going. It’s a special business partnership and a wonderful friendship that was only possible because I went out looking to meet people in my field. I still seek out partners who I can refer work to, as I believe broadening that professional network is often a win-win for everyone involved. Having just returned from Skyword’s content marketing conference in Boston, I can confirm that showing up in person makes the difference in forging meaningful personal connections. It’s always well worth investing the time and effort (and you can always indulge in a little restorative introvert time afterward!).
5. Run your business like a business
Some people labor under the misconception that the writer’s life is a glamorous one. As the daughter of professional classical musicians, I’m here to tell you that’s not the case. Artists struggle mightily to succeed as self-employed entrepreneurs even as they strive to refine their craft, and there’s nothing romantic about it. Perhaps because I witnessed my parents’ business challenges first-hand, I had no illusions about how important it would be to ensure I was running a tight ship when I went into business for myself.
Fortunately, having recently been an IT Director with responsibility for a large organizational technology budget and considerable experience negotiating contracts alongside legal counsel, I wasn’t exactly green when it came to the business side of running my own company. Each year, I resolved myself to tackle one top-level business challenge that, if left unaddressed, would eventually impede my future success. The first year, it was taxes. This year, I’m working an ambitious financial plan under the guidance of my incredible financial advisor, Pam Capalad of Brunch & Budget. In 2019, I’ll set a new top-level business improvement goal.
As I acknowledged to myself early on when starting lowercase d, it is not necessary to be an expert in all aspects of running a business in order to do well. It is important, however, to recognize which business goals you can reasonably accomplish on your own, which ones require training and education, and which ones require the services of an experienced professional or service provider. I’ve never regretted getting the right help when I’ve needed it. It’s enabled me to reach the next level each time.
Now that I am celebrating five years of self-employment, I’m grateful for all that I have learned so far and the terrific colleagues and clients with whom I have the privilege of collaborating. It’s been supremely fun, a lot of hard work, and deeply rewarding. As I open up a fresh, clean page and start writing the next chapter of my business, I can’t wait to discover how I will grow next.
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