The Pros + Cons of Self-Employment

by Carly Schorman

Okay, so you have a lot of talent or a following or a special skill and you’re ready to cast off the tawdry shackles of your “day job” to embrace the American entrepreneurial dream. Maybe? But before you tender that letter of resignation, I suggest to take a tip from a business owner and really think through the pros + cons of self-employment before you barrel your way into living your best life, only to find yourself longing for lunch breaks and dental benefits.

Yes, YabYum might still be at side-hustle status, but when I change hats, professionally speaking, I’m still in charge… which is both a boon and a bummer. And, as the child of serial entrepreneurs, I learned the unsteady terrain of being a business owner early in life and decided that just wasn’t the path for me. And now I have to live the wry twist of fate of that laughs at me every single day.

So, today, I’d like to discuss and maybe dispel some common misconceptions about the joys and sorrows of being your own boss. As you’ll see, few things can be clearly separated into the “PRO” or “CON” category when it comes to running your own business…

1. You Make Your Own Schedule.

Mention this reason to any business owner as a reason for starting your own business and you’re likely to be met with peals of maniacal laughter. Sure, sure, sure, I “make my own schedule” but oftentimes that schedule stretches well past legal limits put in place to safeguard employees from tyrannical bosses.

When you work for yourself, chances are you are acting as your own tyrannical boss. I know I am. And, because my husband is vested in both ventures with me, we get to act like tyrants together – pushing each other to work harder, longer. Weekends get haphazardly canceled. And we’re continually asking family and friends to forgive us for missing gatherings and ignoring social obligations.

I literally told a friend this week that “this year’s looking rough” when asked about scheduling a weekend at a beach house together. It’s fucking June and the whole remainder of the year is scratched when it comes to non-business related travel. We might sneak in a wedding here or there, strictly out of love for family (and familial obligation), but our big travel plans have been put on hold until things “settle down”. Meanwhile, years pass and we’re still waiting for that great settling down we’ve been talking about.

Business owner and budget educator, Suzanne Ryan of T&H Financial Coaching, explains that these days, “It’s not about balancing; it’s about blending.” As an entrepreneur, work blurs into after-hours and weekends and I struggle to find ways to unfurl without the preoccupations of business sneaking their way into my mind when I’m trying to focus on other things, like fun or family.

2. No more bad bosses.

Back when I was working for other people, I had that one boss that would time you in the bathroom. I also had the boss that would make uncomfortable and unfunny innuendos while rubbing your shoulders. And then there was the kinda-recovering alcoholic who kept asking me to invite my (male) friends to stop by while I was working so she could make passes at them. And then there was the randomly-given-to-fits-of-rage guy. Or the filming-porn-after-hours guy. I’ve had so many bad bosses during my lengthy stretch of shitty jobs in high school and college and more college that I literally could do a stand-up comedy special on the horrors I’ve witnessed.

Working for myself meant I was calling the shots. No one could put Baby in a corner anymore. I was THE BOSS. Just as suddenly as I took on the mantle, two very glaring counterpoints came to light to rub the spit shine right off my excitement. The first was rather unexpected, but perhaps you’re familiar with it. I call it the Jar Jar Binks Problem.

Now, for all you Star Wars fans, maybe you already know what I’m alluding to. See, George Lucas came up with the character of Jar Jar Binks as a way to draw in younger audiences. And, because he is George Fucking Lucas, no one felt quite up to saying, “You know what, George, this character is really, really, unbearably annoying. It’s going to throw the whole franchise off its game.”

If you make a bad decision, you have no one to blame but yourself. And, oftentimes, new business owners don’t have the checks-and-balances that comes from working with colleagues to help safeguard you from venturing down the wrong path unless you commit to regularly networking with other business owners. You take on risk and have to own the outcomes, be it victory or disaster.

3. You Do What You Love.

Okay, so I do feel very fortunate to be doing work that I love, but even that can be problematic given enough time. I realized that when I gave into some Facebook venting about being a business owner and was confronted with some at-least-you’re-doing-what-you-love push back. It’s true. I do work I feel passionate about. Both at YabYum and in my other roles, but when the work week ticks past the 70-hour mark or I have to show up on a sick day, I’ll admit I don’t love it.

In fact, I kinda resent it – in a weird, deep-seated way one comes to resent family, with a mixture of love and understanding thrown in to confuse the resentment and keep an acrimonious crust from forming.

Think of it this way, no matter how much you love pizza, you won’t love pizza if you’re stuck eating pizza all day, every day, even when you really just want a sandwich. Even a plain, ol’ PB&J starts to sparkle with unattainable longing. I mean, I really love listening to new music. Do I love sitting down to check 117 submissions on a rainy Tuesday when I only want to listen to Tom Waits? No. As with anything, there are good days and there are bad days.

Work is work. And while I firmly believe it is easier to do a job you believe in, even a dream job becomes a job given enough time and aggravation.

4. You Get to Create the Company Culture.

A couple of the practices I instituted at my business include offering employees “flex time scheduling” and allowing for office slippers. This might not seem like a big deal, but sometimes the little things that can really change a company culture for the better. And, when you run your own business, you can make the rules whether that means pajamas on Mondays or late-start Fridays.

Likewise, as a business owner, you are also tasked with creating a company culture for all of your employees… even the difficult ones. When you think about how much time you spend with coworkers versus the time you spend with friends and family, the numbers can get rather alarming. Being in charge means you have to be the bigger person and set the just course through problematic moments.

Even if you’re a graphic designer, alone with a laptop and an Adobe subscription, or beanie knitter on Etsy, working for yourself often means dealing with clients or customers. As the person in charge, you have to set the tone for a positive experience for all involved.

5. You’re the Chief of Finance.

I pretty much operate at a Woody Allen level of anxiety at all times so entrepreneurship was really not the right path for me. I knew that before I embarked upon this journey and it’s only been reiterated to me time and again. No, I wasn’t pleasantly surprised at how easily I navigated the tenuous waters of small business ownership. Instead, learning the ins-and-outs of ownership revealed a whole new level of stress I didn’t previously know. Largely because, as a business owner, you have to think about irregular or varying income and, if you have employees, you need to make sure you are responsibly accounting for all your costs or someone could lose their livelihood.

Additionally, when things get tight, it’s the small business owner who often bears the brunt of impact. You can’t tell your employee they’re only getting half-pay that week because a contract fell through or skip a workman’s comp payment because your A/C went out. Sometimes sacrifices need to be made during the early days of a new business and, unless you’re a total louse, the business owner is frequently the one to feel the burden of unexpected financial strain.

Thankfully, early in my business ventures, I met with the aforementioned budget expert (Suzanne Ryan) and she helped me gain an expanded view about balancing an irregular income which saved me a lot of woes along the way. But, it can be tremendously stressful when financial ups-and-downs make it difficult to establish a clear outlook on the future.

Of course, at the same time, you’re not selling yourself at some wage slave rate to a faceless corporation. And, when you get to enjoy the boons of a job well done and maybe even a little extra financial float in a good season, you might feel like you’ll never see another rough patch again, but chances are, you will. For many, myself included, being a small business owner means riding the waves as they come which can be both exhilarating and terrifying.

6. You Become a Jack-of-All-Trades.

Ask me what I am and my first impulse is to answer, “I’m a writer.” But is that totally true? Partly true, sure, but when I look at my day planner, it’s hard to consider that an accurate representation of who I am or what I do. I’m a salesman and researcher and publisher and podcaster and efficiency expert and financial consultant and negotiator and social media manager and delivery driver and promoter and a million other things all rolled up into one chaotic week — every single week.

I wear a lot of hats and sometimes it’s hard to keep all the tasks straight in my head… or on my calendar. I’ve had to learn delegation and prioritization and self-discipline. Lots and lots and lots of self-discipline. Because when no one else can do it, and it has to get done, it’s up to me to figure out how we get there.

The variation keeps things interesting but it can be a bit overwhelming too. I feel like I constantly need to be adding to my skill set or risk falling behind. There’s a lot more to running a business than 1099s and saving receipts. This year I’ve had to tackle licensing agreements and client resource management systems. Next year it might be national marketing campaigns or escape velocity in a Prius. Who can really say? The point is, the landscape is always changing and the challenges change right along with it.

It’s hard to get comfortable when you don’t know what’s coming next.

Pluses + Minuses

Owning your own business can be rewarding, financially and otherwise, but it’s best to approach the challenges with your eyes wide open. As with any long-standing relationship, the parts you once loved about being your own boss might someday annoy the crap out of you, but some serious tenacity can help you over the hurdles.

Colleen Malley Schwartz 01