Alrighht. This will be interesting.
Lol can you imagine the most timid writer of all time, starting everything off with that?
“This will be interesting. I promise. No, keep reading. It’ll be good.”
The order here is roughly chronological…
1) Soup Kitchen Coordinator
My first job, ah! The nostalgia. Didn’t make much money here. Idk why this would (ever?) be included in someone’s blog about how to make $$ as an entrepreneur, but alas, these are my roots.
Was it fun? Yes! And not really… Everyone there was committed to being there and wanted to be there. Everyone cared. So that was cool. It wasn’t fun when you had to deny someone help they needed. We had to kick someone out of the transitional housing program when he was caught drinking. Sometimes we didn’t have enough bus passes, even for someone trying to see their daughter.
Did I make money? $200 a month and free housing. Definitely a volunteering program.
Things I learned
- So much inefficiency! - once we literally had volunteers move clothes from one area to another, just to have the next set of volunteers move them back. What!?!?!
- It’s not all about efficiency… - ugh… the most useful thing I did was go to the hospital with a guest whose big toe had to be amputated (diabetic neuropathy - she couldn’t feel that the wound on her big toe was rotting / super infected). It was good just to be there with her.
- Working with and around people who are giving their all is energizing and fun.
2) stand up
Tecchhnically didn’t make any money here. I went 14 times and definitely was getting better! It was a total grind though. It wasn’t uncommon to wait 2 hours for 5 minutes of stage time, and sometimes, you were just performing in front of the other comics, including the ones that just bombed.
Was it fun? Yes and no… Writing jokes was fun! And getting laughs was fun. Bombing was awful. Waiting was boring.
Did I make money: Narrr. Once after a good set, the host asked if I had 10 minutes of material. That was the closest I ever came… Apparently I too eagerly said, uh what yes yes yes I do yes please, because he was like “No you don’t!” And that was probably for the best… I really didn’t have 10 minutes haha. But I feel like if I had just cooly nodded… maybe he would have given me one of the paid, 10 minute slots.
What I’d do differently:
- Find a mic or two just to practice / workshop jokes. Ideally one where you don’t have to wait for over an hour to get up.
- Practice for friends & family! I think it’d feel awkward, but actually be kind of helpful. Gary Gulman practiced in front of kids as a substitute teacher. I feel like I really just needed to practice talking through jokes, and seeing if they were remotely funny.
- After that? Just go to an actually good and fun open mic with a real audience.
3) Freelance Writing
This was the second highest paying job that I gave myself, and it was a lot of work. The writing would usually take me 4-8 hours, depending on what it was, but the real work was getting a piece accepted somewhere.
To get a piece “accepted” you have to email your idea or sometimes the whole essay / article / poem (whatever) to the publication / editor. My acceptance rate was around 1 in 20. Since it would usually take me around an hour to write a pitch, it ended up being about 28 hours in all to get paid ~$200 for an article. Add on the fact that sometimes publications would take a month or two to send you a check, and you can see how this could get pretty dicey money-wise.
Did I make money? Yeah I did. I was able to repeatedly get some articles for the weirdest, most niche magazine of all time (writing about technology to mitigate climate change with a conservative slant?) That was fine. But they pretty much always accepted my pitches, so I pitched and wrote here often. I got $50 for a poem, $50 to write about pizza (a dream come true), and $800 for a personal essay. In total, I want to say I made around $2-3k freelance writing (over the course of like, 2-3 years).
Did I have fun? Yes and no! It was fun to write humor pieces, or essays… it wasn’t super fun to write about the new tech news in nuclear fission or whatever. I got to cover some stories on homelessness in Seattle, which was something that I’d always wanted to do.
Things I’d do differently? Yeah there’s a couple…
- only pitch things I really really wanted to write.
- not rely on it for a primary source of income (at least for the first couple (6) months).
- target high-paying or high-leverage pubs. One pub paid me $800 for an essay. Now that was worth it! Other publications, like the New York Times, The New Yorker, New – anything with New York in the title – will give you writer street cred. So that’s cool.
4) Music
On the street baby. Music on the street. Idk if I can even really say that I tried to do this. I busked like one time. But we did it fam. It was pretty embarassing, I got a note wrong on Silent Night and left haha.
No fun. No money.
What would I do differently? Practice more? Bring a music stand?
5) Data Engineering
ahhh the “real” jobs. I worked a couple jobs as a data engineer. These jobs made me money while I was trying to decide what to do. They were the classic cog-in-machine jobs doing whatever work, which I felt (if I weren’t careful!), I could spend my whole life on by accident.
Was it fun sometimes!
did I make money? yes
Things I’d do differently
- Can I say, not take it as seriously? At least, I wouldn’t let it take over my life, and I’d want to make sure it didn’t take up much of my mental space. Like, don’t worry about work after work, you know?
- Find a way to pursue other side projects (payed opportunities!) Whether it’s before work, at lunch, during work, etc etc. Let the job be your money maker to fund your other shit.
- Enjoy the good parts! There were definitely parts of working in a traditional job that I missed once I left – The getting paid on a schedule part, the freedom to buy things like lunch, the office coffee and chit chat and happy hours.
- Prioritize doing something fun after work so you don’t feel like a total work machine. This is maybe just life advice lol. But for sure, when I was doing freelance stuff in the morning, then working 9-5, it was really important to do something not-work (and definitely fun) after 5.
6) Freelance Developer
This one was cool! I got one contract where I was paid pretty well, and the people I worked with were cool. This was the first time I felt like I actually liked coding. I spent hours and hours making this app, and it ended up being good! I’d never made an app before, so it was all hands on deck, and the original contract was for three months, so we had to go fast! I loved the flexibility, freedom, and ownership I felt while working, and this is something where - if the projects just kept coming, I would keep doing it.
Alas, a big part of freelancing in any field (I learned…) is getting the work, and that’s the part that I wasn’t good at and honestly? Didn’t even think about (until it was WAY too late). I got my first gig from a co-worker, another from a friend, but all in all, I just wasn’t able to spend enough time developing AND getting future work.
fun? yeah! paid? yeah!
If I were going to do it again
- make a plan for how the freak am I going to get more contracts. What am I going to do? How am I going to get sales? I’d probably try to network more, reach out to businesses or potential clients, and… post on linkedin??
- have a backup plan if the projects didn’t come in for a couple months. When would I start applying for jobs? How long could I last without making any money at all?
- Spend some time putting together a website / portfolio and maybe connect that to a social media account where I did lil coding projects just on the side. Could be fun!
7) worked for a sports team
yeaaaah pretty much the coolest job I ever had. Kind of. I was a do-it-all guy, including running our youth sports camps. It was fun, but a lot of work, and it did not pay much. I had this job when I was tanking after the freelance biz tanked, so I loved it because it made ends meet. Thank God. It was cool, though, to be a part of a small team that did a lot of work. I got to manage a social media team! How fun!
The hardest part here was the project management side of things. There were so many initiatives, and so many things that needed to get done (like, 100p had to be done today kind of things) as well as work that we were trying to do to bump our revenue and fan base. Balancing all that was a challenge. Proving to the CEO that I was balancing it well was also a challenge. Fun? At times… Paid, yes.
Things I learned
- buffer exists! It was cool to see a whole social media plan in action.
- the value of having someone who loves what they do and is good at it… we had one social media guy who was just on top of his shit, and good at what he did. That rocked. It was great to work with him, and I think he moved from the “intern” role at this place (unpaid, free labor!) to working for real at a sports team!
- take tough talks on the phone, not on slack.
8) ~ Online Course ~
ughhhh is it possible to get more cringy than this? I literally tried to do this. I tried to sell a freelance writing course. After taking a freelance writing course. What?
Did I make money?? No! ugh! why would anyone buy from you!!
Was it fun?? Okay actually kind of. It took me a solid day to set everything up. Solid like 8 hours, let’s say. And as I was working, it was cool to like, think of the possibility that the whole thing might work. It was an effort to get everything set up. I think the hardest part was getting all my copy right. Like trying to make my email sound good, trying to make my website sound good. Trying to make good ads essentially.
Things I learned:
- it felt really cringy and gross to email everyone that I had an email for
- no one bought it or even came close to buying it. You can set up a funnel in 24 hours with a landing page and a site and everything and there’s a chance no one will buy. I feel like whenever I watch a certain subset of the internet, I get the feeling that a million dollars is just a canva digital product away. And I think that can be true. But… you’ve got to have like… a really good… everything. A good product, good ads, good email copy…
9) Deli man
I worked at a deli during the pandemic after I left my job in consulting. It took me about a month before I learned that I wasn’t going to make money by writing articles on Medium (the first iteration of freelance writing…). I got this job, and decided to write a novel while working there.
Money? yeet
Was it fun? Honestly yeah kind of. It felt good, too – writing in the morning then working at a deli in the afternoon. Like that was a good vibe. I would write, show up and wash dishes for hours, then eventually switch over to making sandwiches and soups and garlic aoili.
Things I learned
- How to wrap a burrito.
- The mayo to garlic ratio for garlic aoili…like, 4 gallons of garlic aoili. (It’s pretty much 100% mayo.)
- They’re gonna want you to come in even if there’s a pandemic and if someone gets sick and you’re worried about them getting you sick. They’re still gonna want you to show up, and if you don’t show up, they’re going to want to hire someone who will show up in that situation.
- Working a job where you are 100% replacable is demoralizing and scary, lol.
- Independent of the job, it takes a while before you’re operating on autopilot / feel confident enough to just be the normal version of yourself at work. The learning phase (of any job (even if it’s working at a deli!)) is a little uncomfy.
10) Uber Eats
I had this job when I was trying to freelance, but not getting enough work. It paid decent, and the hours were flexible, though, you made the most money when you were working around lunch or dinner.
was it fun? Yeah! It was sort of a fun gig! I enjoyed biking around, and it was fun to see knew bakeries and restaurants. I would 100p get one of those big boxy bags if I were going to do this again. Once I had an order of thai iced teas explode in my backpack. The person was nice about it, though.
money? actually not bad. It was like $20 an hour, and sometimes tips made it like $22 a hour, which always felt good. Plus you got paid like immediately.
Things I learned
- Risk! What is Risk! Risk is consequence over likelihood. It only took a couple of close calls with cars to realize that a) I wasn’t making nearly enough money to justify the risk of getting wrecked in an accident b) I’d have to pay out the ass in insurance because I was on Medicaid (pretty sure my deductible was like 12k) and c) if I was going to bike all day everyday then I was exposing myself to the risk of serious injury pretty much all the time.
Going forward
Overall I’m glad I bounced around in my 20s. Sometimes I look back and wish that I’d stayed in consulting and just invested the poop out of my savings. Other times, I wish I’d bounced around more, experimented more. So I probably did okay - right in the middle! Final takeaways:
- money matters (ick) - the times that I struggled the most were those where I didn’t know where my $$ was going to come from. A personal rule: if you can’t buy spinach without looking at the price, you gotta make more money.
- risking your health for $$ don’t make no sense.
- having autonomy + ownership over your work is an easy way to make it more fun and meaningful.
- working with people who care about their work is an easy way to make it more fun and meaningful.
- community is important - at times I got crushed by the loneliness of freelancing. The routine of going into an office and the sounds of office banter are soothing.
- it’s possible to spend a full day making an autonomous funnel and not make any money. Ha!
Sooo i wrote this whole thing because your twenties are supposed to be a testing ground. The premise is: try 12 things and fail at 9 of them. I tried… about 12 things! I had some success at freelance writing and programming. I’d say I truly found sucess as a soup kitchen coordinator and data engineer. So it looks like I’m going to be a data engineer for a soup kitchen. Lit.