There's no virtue in forgoing vacation

One of the great ironies in my life — to me — is that I have a financial adviser. Please! Show me where to put my nickels! But I don’t understand how savings plans work, nor do I believe in learning skills that other professionals have and can be paid for (a conversation for another newsletter). So I signed on with an adviser who — once a year — explains where she is putting the money in my IRA while I nod and black out.

I bring this up because the first time I met with her, she gave the sort of rote but appreciated advice that all those folks presumably do: the importance of paying off loans, why you should always have liquid cash, probably something about understanding the stock market (I will not!). Then she hit me with, “If you forgo your daily Starbucks, think of how much you could save!”

FIRST OF ALL. Starbucks??? My friends in Christ: Starbucks coffee is aggressively not good, and I have roughly 80 local coffee shops within a 15-minute walk from my apartment. Should I choose to blow my hard-earned cash on lattes, they will be from an independent shop where the 22-year-old twink barista won’t stop earnestly singing along to Sugar Ray and I am diligently filling out a punch card to receive $10 off a bag of beans.

I understand the point my adviser was trying to make: That forgoing sometimes-frivolous purchases can allow you to put those Abe Lincolns toward something much greater. And I do appreciate that she withheld from asking me not to have avocado toast each morning — a forever-favorite financial warning to millennials.

In addition to my coffee habits (I make it at home 95% of the time, for the record), my adviser also didn’t know another very important bit of info about me: I am hyperfixated on earning. No need to warn me about having enough! I have already accepted every freelance assignment I have time for, and then some.

I’m not trying to grasp toward an early (or any) retirement, nor am I planning to buy a house (what am I, a sultan?). I am simply sick in the head because of self-employment. When I started working for myself, I heard a choir of fellow freelancers sing the tales of You Just Never Know: Sometimes the work dries up, sometimes you have to fight to get your invoices paid, sometimes, sometimes…

From the very start, it was my understanding that I should never expect a steady stream of work, nor should I expect on-time payments — and therefore I should always be working. For better or worse, my work has only increased over the last four years (and I added a twice-weekly newsletter to my pile, lmao), but I haven’t shaken the notion that the well could dry up at any moment.

“I have to admit, this is probably the first summer in all of my entrepreneurial career that I just can't give a fuck. I feel like I've actually enjoyed my summer, which I haven't enjoyed in a long time.”

Gabrielle Stepan, an esthetician and owner of Bespoke Esthetics Chicago, has worked for herself since 2019. We’ve chatted (vented) before over the state of self-employment, and she — like myself and many others — has been hesitant to take time off because WHAT IF the money dries up?

She acknowledges that a big catalyst for her slowing down this summer was her health, her body quite clearly telling her she needed to chill. But it also made her realize that she didn’t necessarily have much to show for grinding herself to a pulp — even if it was in the name of protecting her future or hitting the next benchmark: Meet this goalpost and expand to a bigger space! Meet this next goalpost and hire a bookkeeper!

But Gabi also mentioned something that likely rings true for a lot of independent workers: She feels judged when she isn’t working. When you work for yourself, it can often feel like you have something to prove. It’s assumed, when you’re employed full-time at a company, that you’re doing the Right Amount of Work — because you have a boss to ensure this. When you work for yourself? Well, who’s holding you accountable?? It couldn’t possibly be the same person who just chased a brat with a hot dog and two bags of chips. No way this person who has as much self control as three toddlers in grandma’s pantry is going to sit her ass down for eight of the good lord’s daily hours to send emails!!

AND THEN, Gabi said something that really blew my mind: “Just because we don't earn PTO doesn't mean we haven’t earned time off.”

When you start working for yourself, everyone has advice on advocating for payments, for choosing business software, for filing your estimated taxes. Very rarely have I heard anyone talk about coming up with your own vacation plan. HoneyBook, a business and financial management platform, released a survey in 2019 that found that 92% of freelancers work on vacation — literally trying to pay themselves in real time for the “time off.”

Gabi and I talked about what it would be like to come up with a PTO calculator of our own making, how it could potentially reduce the anxiety or guilt of actually stepping away from work. I realized how much I’ve never shied away from asking an editor for more money, but I stumble all over myself when I announce I won’t be available for a day or two — often, stupidly, saying I can be reached via text if needed (WHY??). 

“People say, Oh, it must be so nice: You get to make your own schedule. You can take time off whenever you want to,” Gabi says. “And I'm immediately like, Yeah, but I don't get PTO and I don't have benefits. When I'm not working, I'm not making money, and if I get sick, who's going to stand in for me?”

We both agree that working for ourselves still has far more benefits than drawbacks, namely because neither of us is eager to return to a more corporate environment and all the politics, team building, and in-fighting that it entails. But it doesn’t mean the hustle culture of self-employment hasn’t warped our brains into thinking we should never, EVER throw up the “Gone fishin” sign.

“This slow down for me was very necessary, and it is teaching me a lot,” Gabi says. “It's teaching me a lot of patience, but it's also teaching me that I actually miss working a little bit more when I'm feeling good. I don’t mind working weekends. I don't mind working late nights. I only mind it when I'm feeling so worn out.”

Well isn’t that the rub: We start working for ourselves because we found something we truly enjoy doing and want to make it on our own — we legitimately like the work! — but then we wear ourselves so thin that we lose our passion for it. This may seem obvious but when there’s no HR pressuring you to use your PTO before it runs out, it can actually become harder to hold yourself accountable for recuperating. 

I’m taking a fairly lengthy vacation (by American standards) this year. I knew it was time to cool off on work a bit when, recently, I had a big snafu occur with a project. Lying in bed, stressing about it, I thought: What’s the worst possible outcome? They drop me as a freelancer? 

That actually sounded like the best case scenario.