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 our transitional housing program when he was caught drinking. Not being able to give a bus pass to 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. She had Diabetic neuropathy and couldn’t feel that the wound on her big toe was rotting / super infected.

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. Closest I came was after a good set, the host asked I had 10 minutes of material. Apparenetly I too eagerly said, uh what yes yes yes I do yes please, because he was like “No you don’t!” And it’s probably for the best.. because I really didn’t haha. But I feel like if I just cooly nodded… maybe he would have given me one of the paid 10 minute slots for that mic.

Thing I’d do differently:

• Find a mic or two just to practice / workshop jokes
• Practice for friends & family! I think it’d feel awkward, but actually be kind of helpful. 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 one was tough! This is the second highest paying job that I gave myself, and it was a lot of work. Writing the piece itself would usually take me 4-8 hours, depending on what it was, but the real work (for me) was getting someone to pay you.

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 1/20. 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.

Did I make money? Yeah I did. I was able to repeatedly get some articles for the weirdest, most niche newspaper of all time, writing about climate change tech. That was fine. But they pretty much always accepted my pitches, so it was a free $200. I got $50 for a poem, $50 to write about pizza (dream come true), and $800 for a personal essay.

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

• 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 pubs, 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. It was pretty embarassing, I got a note wrong on like silent night and left haha.

No fun. No money.

6) Data Engineer

ahhh the “real” jobs. These were the jobs that made me money while I was trying to decide what to do. Definitely made money here, lol. But it was classic: cog in a machine, whatever work that I’d end up spending my whole life on by accident.

Was it fun sometimes! did I make money? yep… Things I’d do differently

• Can I say, not take it too seriously? At least, don’t let it take over you life. Find a way to pursue side projects in the morning. Let it be your money maker to fund your other projects
• Enjoy the good parts? The getting paid on a schedule, the freedom to buy things like lunch, the office coffee, the office chit chat and happy hours
• Prioritize doing something fun after work so you don’t feel like a total work machine.

7) 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 an app, and it turned out pretty good! I’d never made an app before, so it was all hands on deck, and we went real 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 is getting the work, and that’s the part that I wasn’t good at and honestly, didn’t even think that I’d have to do… What?! Looking back it seems so stupid. Of course you’re going to have to get work!! Ugh. The first gig I got was from a co-worker. After that, I got another contract from a friend, but all in all, I just wasn’t able to spend enough time developing AND getting future work.

If I were going to do it again

I’d want a better plan of a) how the freak am I going to get ocntracts. Literally, what am I going to try to do to get people to pay me to code. And b) have a backup plan if the projects didn’t come in for a couple months.

I’d also spend some time putting together a website / portfolio and maybe connect that to a social media account where I did lil coding projects on the side. Could be fun!

8) worked for a sports team

yeaaaah pretty much the coolest job I ever had. Kind of. I was the do-it-all guy, including the camp counselor for our 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 was slowly dying, so it was good to just make ends meet. But ultimately it was so much work, and I wasn’t getting paid very much. Pretty quickly needed to eject out of this one to find a higher paying job.

9) ~ 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.

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 no one m

10) Deli man

I worked at a deli during the pandemic, after I left my job in consulting.

11) Uber Eats

Truly learned the meaning of risk here… It only took a couple of times of almost getting railed by a car to decide that 1) I wasn’t making enough money to justify 2) if i got wrecked in a car accident, I’d have to pay out my ass in medical bills (since my deductible was like 12k on my shitty health insurance).

But! It was sort of a fun gig! I enjoyed biking around, and it was fun to see knew bakeries and such. I would 100p get one of those big boxy bags if I were going to do this again.

*kidding!**

**kind of