Confession: The Fact That You Work for Yourself Makes Me Feel Bad

Confession: The Fact That You Work for Yourself Makes Me Feel Bad

Oh yeah, you're so cool sitting in that coffee shop at 11am or "just catching" a movie matinee on a Wednesday. You're doing you, working for yourself, and you're doing it in style. But what about me?

I'll start this article by assuring you there won't be any entrepreneur bashing here. In fact, there's something pretty incredible about a whole generation that grew up believing anyone can have a great idea and that if you work hard and throw yourself into it, that idea can turn into a viable money-making machine. Couple that with the fact that many of us want to make the world a better place, and you've got the foundation for startups and companies that will do great things. There's no question—we're changing the world, one Kickstarter campaign at a time.  

But for every great concept turned startup business and for every entrepreneurial project that launches and makes millions, there's someone working as an office assistant, a marketing manager, a financial analyst, or a receptionist who isn't calling her own shots. She's one of a team of 20 or 50 or 1,000. She commutes along with countless others working jobs just like hers. And (hopefully) she likes what she does and the way she spends her days. But the thing about this entrepreneurial-centric culture is, sometimes it feels like that's not OK. 


If you spend any time listening to podcasts or scanning websites dedicated to career advice, everything seems to point back to entrepreneurship. 

Here's How to Turn Your Side Gig into a Full-time Job. Beyond the 9-to-5: Discovering Your Passion and Making It Work. 5 Steps to Becoming Your Own Boss. 

Common themes with a decidedly DIY tone—and precisely the sort of advice that breezes over any careers that started with "I don't know. I saw the job listing, and I thought I might be good at it."

For every person who launches their own venture, there's another one of us doing a pretty great job holding down the fort by supporting teams, bosses, and leaders. Where are the accolades for that? 

If you need someone to give you the budget you'll work with or a deadline or a performance review to keep you on track, there's nothing wrong with that.


The words applied to people who don't go it alone aren't always that pretty. "Risk averse." "Traditional." "Boring." By comparison, you hear entrepreneurs talk about themselves as people who just "couldn't handle the daily grind." We get it. You don't like confines.

So we've got the freelancers and entrepreneurs taking risks and zero prisoners. They're giving interviews and writing blogs about their experiences. They're writing books, too. They're aspiring to reach "serial entrepreneur" status with past companies, not positions, smattered across their resumes. 

It's a cool life if you can get it. But then again, what if you don't want it? Cue the new working girl. 


There have been times over the years when I've fantasized about going full-time freelance. Certainly, the appeals of working from my bed until noon or meeting friends for a leisurely lunch haven't worn off. And on those occasional days when I do work from home, I've been known to not get dressed all day. It's glorious.

But the thing of it is, a few hours of that and I want to go back into the office. I like collaborating with people and teams and having someone hold me responsible for my actions. Sometimes? I even like being told what to do. Maybe you do, too. {click to tweet}

For those of us who prefer "traditional" careers (a squirm-worthy term, I know), it's not because we lack the ability to come up with great ideas, persuade others, or take leaps of faith (although if you prefer to play it safe with your career, that is OK). It's that if we've learned anything over the past decade, work doesn't have to look or happen any one way.

Our generation's tendency to rebel against the traditional workplace is well-founded. The 1980s cubicles of Working Girl and 9 to 5 are the stuff of pop cultural legend. Then there was that claustrophobic idea that you had to "stick it out" in one career or company until age 65. Don't even get us started on jobs that require "clocking in and clocking out."

But if the freelancers and entrepreneurs have proven one thing, it's that we can pick the way we work and how and when. And just like they rejected the sort of formalized work they hated in favor of coffee shop brainstorms and agile meetings, if you like working out of a corporate office or as a line cook or barista or customer service rep, you can.

You really can.

If you need someone to assign you a budget or a deadline or a performance review to keep you on track, ain't nothing wrong with that. {click to tweet} All it means is that you know the best style of work for you

I've had horrible bosses, but I've had great bosses too, the sort of women who turn into mentors and friends. I've worked at corporations and startups, in art museums and behind coffee counters. I've completed great freelance projects and cried over nasty freelance clients. Inevitably, I've questioned whether I would ever find the career that was "right for me."

There's no right answer, of course, and no perfect career course. Every good entrepreneur knows that for every venture that goes viral, there are countless bad ideas and failed businesses. For many, there will never be a success story. So we all have bad days, regardless of whether we make our own schedules or answer to a timesheet.

The freedom of freelance sounds great when you're sitting in commuter traffic with no end in sight. But then there are those days, especially sunny Friday afternoons, when I like knowing that when I leave the office, my work stops, too. It's not as glamorous as building the next million-dollar-making app, but it's good work if you can get it. And I'm OK with that. So to all the solopreneurs, side hustlers, freelancers, and self-made millionaire freaks, I salute you. But now I'm going to head into the office and do me, too.

Are you a proud worker bee? Tell us your own story in the comments.