The 10 Big Money Questions With Josh Gondelman

In this latest edition of the 10 Big Money Questions, we’re doing something extremely daring and possibly even controversial — we’re talking to a boy. A boy! Yes, I know, the overall point of this series is to talk to extremely smart and cool women about their money lives, because women don’t talk about these things nearly enough. But I like to consider myself an open-minded person, and you know what? If the boy is cool enough, and smart enough, and has enough to share with the TFD community at large about all things money, why not?

And I’m pretty sure that, if you don’t already, you’ll love Josh Gondelman as much as we all do. In addition to being a prolific stand-up comedian (who is releasing a new album very soon!), Josh is a writer for Last Week Tonight with John Oliver (!!), a humor writer, the co-author of Seinfeld Today, one of Brooklyn’s most influential people, and arguably the nicest person on the internet. Josh combines the prolific comedic output of Weird Twitter with the social skills and kindness of Self-Help Twitter, and the result is nothing short of wonderful. Josh is the sort of guy to give you a pep talk out of nowhere because he sensed you needed one, and he isn’t doing it to get something from you later, which is essentially unheard of for someone who has to promote their work online. He’s an incredibly hard worker who does a lot of very cool things, and he is the perfect Inaugural Boy for this series.

And, without further ado, here are his innermost thoughts about money.

What was your relationship to money growing up?

I definitely knew it existed and was something I did not have unlimited access to. I was lucky to grow up in a home where my parents shielded me from the real anxiety of any specific financial concerns there may have been, but I also grew up knowing like some things cost too much money to have, not just in terms of high-priced luxury items. I didn’t always know exactly what that threshold for “too much” was but I knew like…going to restaurants is less financially sustainable than cooking, and it makes financial sense to get ice skates at the secondhand sporting goods store. I’ve always been conscious of that. It took me a long time as an adult to upgrade from Old Navy jeans to Gap jeans.

Do you feel, looking back, like you got a good education about money, either at home or at school?

My parents are really lovely and generous people, and they’re also very sensible about money and taught me what I’d consider great priorities in terms how how to spend money, even just in terms of like…don’t blow it all if you can afford to save some for the future. And, make sure you have health insurance. My understanding of finance is incredibly limited. I wish I’d learned more about that in school. I know a lot of finance words but not necessarily what they mean. It’s the same relationship I have to a lot of popular tv shows. I know there is something called a stock market and something called Pretty Little Liars but I don’t know if I can use either one to make my life better.

If you have debt, what are your strategies and philosophies for paying it down?

I’ve (again) been fortunate not to be in any large-scale debt. When I owe money to a person I try to pay it back as fast as I can, out of politeness, but with bills and stuff I always end up waiting until the last possible day for no good reason. I am a terrible procrastinator with tasks that take almost no time to complete. So I’ll put off paying a parking ticket because I don’t have a solid hour, even though it’s a 90 second process on the website. Then I remember weeks later that I never did it and frantically try to find the ticket or bill before I start accruing penalties.

What is your current job (or jobs!), and how did you get to where you are today in your career?

I’m a writer for television and a standup comedian. I got to that point by doing lots of standup comedy and writing for little to no money for a long time while I worked in education (teaching preschool and tutoring for standardized tests), which I also liked very much.

When was the first time you negotiated for yourself, at work or otherwise? Can you tell us a bit about that?

I’m getting better at negotiating, but I used to be very bad at it. My first ever negotiation was when I was a kid, and my parents and I were discussing the possibility of me getting an allowance, and I had read about allowances in a book from like the 50’s or something, so I had no idea what a reasonable amount to ask for was, and I requested twenty-five cents a week. My dad kind of shook his head like: “It would be convenient but unfair for me to accept this offer.”

What is something you understand about money now that you wish you had before you graduated from school and entered the “real” world?

Honestly, I wish I’d gotten a credit card at a younger age to use for small purchases and help me build credit. Also, I wish I’d started paying someone to do my taxes earlier. My returns are always a mess because I’ve always had a bunch of different jobs, and I didn’t realize like…oh…this will pay for itself almost immediately because I have no idea what I’m doing and a professional person will do this better.

What is one of your biggest money-related mistakes that you’ve made? What did you learn from it, and what do you do differently now?

Being kind of sloppy and late with tax stuff for a year or two when I was freelancing and tutoring and doing standup on the road. My big takeaway was that it’s okay to ask for (or pay for) help if you need (and can afford) that to stay on top of things. I honestly didn’t know how much it would cost to do that or where to go, though. Last year my girlfriend was like: “Oh I know a great tax preparer.” And I went to him, and it was a visceral relief. I should have just asked around or looked up how to do that before, though.

What is one big financial goal you still have for yourself? Are you currently using any concrete strategies to pursue it?

I’d like to be better at putting some amount of money away for retirement consistently, which I’m doing now! But also like…opening mail from my bank. I’m a really anxious head-in-the-sand type when it comes to things like that. If I’m struggling financially, I keep track of things pretty closely, but when I feel like I have enough money for the time being, I am less vigilant. It’s kind of a bummer to scrutinize my bank statement and realize how much money I’ve spent on grocery store sushi in the past month, for example. I’m trying to be better at monitoring those smaller things and fiscally looking myself in the face instead of avoiding eye contact with myself.

How do you deal with financial setbacks when they happen?

There’s definitely some battening down of hatches in terms of lowering my overhead and limiting frivolous expenses. Then my next thing is to seek out more work, which is a helpful impulse but not the best one. I should get better at that first thing more consistently so I don’t feel like I have to take on extra gigs/tasks when unexpected expenses arise.

What is your personal definition of success, and do you consider yourself successful?

This is a big question. I think using the word “successful” feels like: “Okay! I did it! I’m a success now! Look at me, world!” Anyone who can confidently say, “This is where the magic happens!” about their bedroom is successful in my book. I definitely do not feel that way. The past couple of years, I have been very fortunate to make a living in a fulfilling line of work in a way that seems like it could be sustainable both professionally and personally. For a long time, I felt like my professional successes were at the expense of my personal relationships, and to be in a place where I can have a career and also be a present, engaged boyfriend and dog parent. That’s really satisfying, and I’m incredibly grateful to be in that position right now.

Follow Josh on Twitter here.