7 Things That TOTALLY SUCK About Self-Employment

#WorkFromHomeDay!!!

Privilege is real. When I first graduated from college, I was definitely not in a position to "start my own thing." I had few savings, I lived in an expensive area, and I needed a job that would pay me now. I couldn't afford to "start something" that would probably fail, and definitely not be profitable for at least few months.

So I took a job at a startup. It was a daily deal site, like Groupon. And, like Groupon, it spent a lot on advertising. My daily ad spend was $13,000 -- and I didn't even know enough to know that was absurd. 

By the time that company ran out of runway, I had enough savings that I finally was in a position to "start my own thing" -- and it's been awesome!

​I run Paved With Verbs, a college counseling and life coaching company. There, I've had the opportunity not only to run my own business; work with amazing students from around the world (most of my students are based in the Bay Area of California, but I also have students in Chicago, Florida, Texas, New York, and even China, South Korea, Vietnam and the Philippines); and travel for three months per year...

Playing ping pong and talking about Katy Perry at a monastery in Mandalay, Myanmar.

But I've turned something I'm both passionate about (playfulness and gifted education) and good at into a career. According to Andrew Yang, founder of Venture for America and author of Smart People Should Build Things: How to Restore Our Culture of Achievement, Build a Path for Entrepreneurs, and Create New Jobs in America... it's actually pretty rare for people to do this. Lots of people, he writes, dream of "starting their own thing" and "making the jump," but few ever do.  

But it's not all butterflies and roses. A text I got this morning reminded me that there are at least five things that totally suck about self-employment -- and if there are others I've missed, definitely let me know in the comments.

1. Your grandma will never understand exactly what it is you do. 

I've previously written that I don't feel very sensitive to what others think of me. I've even shared 3 Scientifically Proven Ways to STOP Caring What Others Think and Live a Happier Life. (Even though, truly, the only way to entirely not care what others think is to be a psychopath.)

But... 

I still want my own grandma to be proud of me.

And it's unclear whether she is. 

Almost every time I talk to my grandma, I have to explain what my job is. I have to explain that I actually make money. I have to explain what a blog is. I've even told her my hourly rate, which is listed very clearly on my website. (Some admissions tutors don't list their prices. I believe in transparency.)

Nevertheless, she still always has this confusion and attitude about what I do. Once, she even suggested that I go and ask my other Stanford friends for jobs at their companies. It's hard to get mad at a little old lady, but that was pretty insulting. 

2. Your taxes are way harder than everyone else's.

From my perspective, no one who's a W-2 employee has any right to complain about their taxes ever. I mean, unless you've got some complicated real estate investment in another state or something. Then I suppose you could make a case...

Yes, TurboTax helps. But you probably got to just bought the normal, $30 one. I had the buy the Home & Business version, which is 2-3 times more expensive. Yeah, that's only $60 more -- but still​! 

Similarly:

3. The money doesn't just magically show up in your bank account -- you've got to constantly negotiate, invoice, and force people to pay you.

I miss the days of direct deposit, when I did the work and then the money would just appear in my bank account.

As a small business owner, you're constantly explaining your pricing, getting people to sign contracts, and, sometimes, even hounding people to pay you. 

When I first got started, I was burned a few times. I learned from it. I changed the way I run my business. But even so. I still have to write up invoices for my customers who go hourly, instead of full-package. I still have to nudge, and then nudge a little harder, and then a little harder, sometimes.

That's part of running your own business. You've just got to accept that:

4. Whenever you're not working... you could be working.

I spent last winter traveling in Central America.

I spent this winter traveling in Southeast Asia and Sri Lanka.

That was wonderful, and a big part of the reason I'm doing what I'm doing.

But the thing is... when you run your own business, the work never actually stops. At any given moment, you could be working on your company. You're at the gym. You could play another game of basketball...

But you could be blogging. You could be advertising. You could be invoicing. You could be editing essays.

Once in a while, I feel a flash of envy for people with their cozy 9-5's. 

6. It can be super isolating.

So I'm, like, super into songwriting right now. Okay -- I'm, like, a little into songwriting right now. And I'm working on a song called 1099. It's about how isolating it can be to work for your yourself.

You people with your direct deposit and your grandparents who understand and respect what you do for a living... also have water coolers. And in-person meetings. And regular, unplanned interactions with other people like you. And "work friends."

I love what I do, and during my busy season, I do a lot of in-person, emotionally intense work. But... there are a lot of days when the first person I talk to is the person I order my burrito from at 6pm. 

And sometimes, I take the burrito person off-guard by being like, "I'll have a super burrito carne asada. BLA BLA BLA BLA BLA BLA BLA."" The words start pouring out, and I can't stop.

It's kind of funny. But it's also kind of pathetic.

7. Just because you have some flexibility in your schedule, people assume you're, like, unemployed or something, and you can just hang out with them all day.

It's not that I don't appreciate the invites. We all need more friends, right? (I mean, I did just complain about the social isolation that accompanies self-employment.)

It's just vaguely insulting when people think you're, like, free to hang out with them all day on a Monday. Like... do you not understand that I'm running a business? That I don't just hang out and do nothing all day?

Do I travel a lot? Yes. Do I play a lot of basketball? Yes. Do I join frisbee leagues, enter songwriting contests, mountain bike, and make epic weekend plans? 

Totally.

That's because these thing are important to me, and I make it a priority to have fun and stay active. 

Besides, as I wrote in The Best Productivity Hack in the WHOLE WORLD... Is THIS One, making plans forces you to be productive. And when, at any given moment, there are so many things you could be doing that it's easy to become paralyzed by indecision, those plans and deadlines are crucial to staying on top of your game. 

​So, yes. I appreciate the invitation. Just not the insinuation that I totally don't have anything important to do in the middle of a work day. I mean, do you ask your W-2 friends that?

***

Then, of course, there's other stuff. Yes, people who work for themselves often make much more per hour than their peers. But their work doesn't come with benefits or stock options, so it kind of evens out. Yes, I get to write a lot of my travel expenses off of my taxes... but people who work for companies can expense costs on the company card. 

I'm in no way saying that you shouldn't​ chase your dreams. I agree with Andrew Yang: smart people should build things. I'm just saying that there are some drawbacks to freelance, contract, and self-employment. Business ownership is hard. Does it sound like it will work for you?

Then awesome! Go do it! 

​And, of course, if you're already working for yourself and you've got a pain point I've missed, share it in the comments! ​