Self Employment Tips from Someone Who's Doing it Fine

And I mean "Fine" as in, "That's exactly how you're doing it"

A few weeks ago, someone asked me for any tips I might have on organizing, motivating and generally going about life as a self-employed person. This is actually something I’ve been meaning to talk about publicly, as I think I am highly qualified because I am generally quite middling. And I mean that generously and lovingly to myself, but I am sooooo run of the mill motivated, garden-variety ambitious, probably-should-take-15 MG XR-of-Adderall-but-can-survive-without, average. Even so, thanks to a lot of luck, privilege, and consistently applied pressure, I can pay my rent with money I make from a job I invented. There’s a lot of success left on the table, but I’ve crossed that first hurdle. I’ve learned a bit and I’m here to share, if they resonate great if not well congrats you’re better than me, ok!!? Here are some lessons I’ve learned in no particular order for other Type-B’s who have a dream, but maybe lack the obsessive hustle that often typifies successful entrepreneurs.

If You’re Just Starting to Consider The Self Employed Life:

1. Maybe now’s not a good time: One of the first jobs I had when I started stand up was waitressing. I think I’d just seen it on TV, what you do when you want a job in entertainment is get a job as a waitress.So I did that. However, I quickly found out most people eat at restaurants in the evening, and the evening is also when most open mics are. So I had to pivot. My next day job was teaching preschool. This seemed perfect because in addition to getting out early each day, I’d have holiday breaks and all of the summer off. My 9 month salary was divided into 12 months of checks, so effectively, I’d have paid 3 months off to work on my true passion. That first summer, I accomplished nothing. I wanted to write and shoot a sketch, but I was so insecure I ended up throwing it out after looking at it for months. I also lacked the discipline and general know how. I don’t know how to better say it, I had all the free time but wasn’t even sure what to do with it. I’ve spoken to other people that have had a similar experience. Sometimes when you’re fresh out of college and willing to live your brokest it feels like “when would be a better time than now” to throw everything at the wall and try to make a go of your dreams. But I’m here to tell you, actually maybe later! This is not to discourage, if you feel the right path for you is to give 100% on day 1, go for it! But if you gave yourself 6 months after school to make things work and found yourself flailing, don’t worry so did I. There’s a lot of emphasis on youth, but look at Michael Che and Sam Jay. They showed up later in the game with a better sense of self and were able to work smarter not longer. Feel free to give yourself some time to learn the game before you try to go pro.

2. Don’t quit your day job: The single best decision I made for myself pre CMBC was getting a well paid assistant job. I think there’s an instinct to do freelance or part time work when you’re in a creative field, but for me finding a job that was well paid where I could easily take time off and had a consistent schedule was much more conducive to working on my personal projects. I also am someone who believes, the more I have to do, the more I get done. Back in the day I was waking up at 6, working out, going to work, hitting mics, shows, recording my podcast. Now I’m like struggling to post a Tiktok. When I started with stand up I thought I needed to work part time because at any moment Hollywood would come calling and I’d be needed for my big break STAT! It took years for me to need a flexible schedule, and having a day job put a premium on my free time that made me value it more. Also, the amount of brain space I got back by not having to worry about how to pay rent, how to pay to get to a comedy festival, how to pay to upload my RSS feed actually saved me more time than I lost to the 40 hours a week.

If You’re Already Full Time: Here are some tips that absolutely help me be my most productive self. I don’t always do them, but if I’m ever lost this is what anchors me back.

1. Make your to do list yesterday: If I wake up and don’t already know what I’m doing, I’m cooked. The possibility of getting distracted while combing through emails trying to make the to do list are too high, and I lose the day. If that sounds pathetic well it is. I’m a pathetic loser!! That’s why I have any authority to give advice because if even I can do it, then you can too. Make your to do list the night before, while you’re still percolating with all the unfinished tasks of that day. It’ll help you hit the ground running tomorrow.

2. The 2 Hour Rule: My biggest piece of advice would be “to call it.” To call it is basically to admit to yourself absolutely defeat. Sometimes, it’s just not happening today. The best thing you can do on any given day is what needs to be done. But sometimes you just can’t. The next best thing that you can do is something else that needs to be done. And if you can’t do that either, do nothing. But the worst thing you can do is not get anything done but sit at your desk looking at your computer feeling bad about it. That’s what will cause you to burn out. So my advice is, if after 2 hours you can tell you’re making no progress and no progress will be made, just move on. If you can’t get your work done, then do your house chores. If you can’t get your house chores done, do your fun errands. If it’s really just not a day for you, call it. The thing about working for yourself is days are made up. If it’s a bad Tuesday, call it a Sunday, and then make it up later. The important part is making it up later, but you can align your schedule with your energy. It’s better to have rested and reset than to have spent all day hating yourself only to wake up the next day more anxious and upset than the day before.

3. Put your phone in another room: This feels pretty 101, but seriously the way I use my phone as a crutch for anytime something’s a little hard is astounding. It’s a compulsive physical response for the moment I can’t think of another sentence to write, or the clip isn’t working, the book got boring. The amount of time I lose because every hard moment is met with self-soothing phone time is absurd. Just put it out of reach.

4. Stay accountable: I’m lucky that I’m in a partnership where there’s literally someone else I have to be accountable to. And I’m lucky my product requires a weekly scheduled output that keeps me on track. But for the more ambiguous projects and less important habits, it can be so hard to stay diligent. I’m someone who needs external accountability so I have to make it up myself. Find a friend and have a weekly call where you share your weekly goals/ to do lists, and then every week say out loud what you did or didn’t get done. Of course there’s no real consequences besides your own self sabotage when you’re your own boss, but the shame of hearing yourself out loud every week say “I still have to do that” should kick you into gear. Use the audience judgement!

5. Work within your own system: Similar to the Two Hour Rule, there are some things in life you can’t Mel Robbins your way through. Of course, you can always grow and change and get better, but sometimes you have to accept your own limitations (and strengths.) A lot of my professional issues are too grand and overarching for me to fix without hiring a team, but one of the smaller issues in my life is laundry. For decades, I’ve been doing my laundry, folding the clean clothes, and then not putting them away. This causes a cycle of running out of clean clothes, having to do a second load of laundry, having to dump out the clean laundry on the floor to make room for the new clean laundry, creating a mess, feeling overwhelmed. In theory, putting the clothes away immediately would fix everything but sometimes it’s just not that easy! So instead of living in a pile of my own clean clothes, I got another laundry basket. Sure the clothes are still not in drawers but at least they’re in baskets and now my floor isn’t covered and I can do other things with all that time I saved not putting my clothes away. Sometimes the problem is you and you can’t be solved, so build a crutch. If you can’t fix the problem, mitigate the fall out.

6. The thing that’s coming easily to you is probably your strength: One of the parts of a day job that’s so nice is that someone’s telling you what your lane is. There’s such an obvious thing you’re supposed to do. Then you’re on your own and the sky’s the limit and that’s a nightmare!!!!! Sky is everywhere! What direction do you go? I’ve learned is that if there’s something that’s easy for you, it’s not because it’s inherently easy and stupid but because that’s probably your strength. Early into my stand up days I was making very little progress in any direction but was doing radio often. I was a frequent guest on Nikki Glaser and Jim Norton’s radio shows on SiriusXM. I remember once I was on Nikki’s show lamenting my failures, saying I’d never accomplished anything when she responded “well what about the fact that you’re doing my show right now?” It was an important lesson in the peril of self-deprecation (sometimes insulting yourself is actually pretty rude to the people who choose to be around you!) but didn’t click in my mind about where I’d end up in the comedy world a few years later. At that point I was still dead-set on getting into TV writing (which made no sense since I hate sitting alone and writing), but looking back it makes sense that the few credits to my name predicted where things would end up. At the time I used to deny any talent for podcasting because I was sure “anyone on Earth can just talk for hours” but I’ve since found out actually no, not everyone can. So follow your natural talents, allow them to flourish, and if you' feel frustrated because your natural talents aren’t exactly aligned with your hearts desire, I’ve got one last tip.

7. Bonus round for creatives: You will always have a day job. Something I’ve been working on is the pressure I put on my major income source to also be wholly fulfilling. In my life, my podcast is my business and my stand up is my passion. For a while I tried to find creative fulfillment solely from the podcast and in turn I tried to hold my podcast to the same standards as my stand up. It’s only hurt both the success of the podcast and my sense of self. I used to have no problem seeing my admin day job as the financial fuel for my creative self, but now that my hobby is my career, I hold my career to a different emotional standard. I’m sure there are a few artists who live comfortably in NYC off their uncompromised artistic vision, but I don’t think it’s many. And for every one, there are 100 creatives doing a brand collab to pay their rent while they work on their anticapitalist paintings over the weekend. Not every part of your career or every project can fulfill every need. I’ve started to think of myself as an old movie studio, you need to have the blockbusters to pay for the indies. Find the synergy of the multiple prongs of your career, and remember that everyone’s a multi-hyphenate now.

   And for Anyone Going Anywhere

   Bonus Bonus Manifesting Round: Tips from a success: Years ago Rachel Sennott showed me one of the methods she uses for goal planning. Write down all of your 5 year goals. In 5 years where would you like to be? And go crazy, look at Doechii she went from fired from Chipotle to the Grammys in 5 years. It’s a lot of time and anything can happen. Based on those goals, what do you need to be happening this time next year for you to be on the path towards them? Write those milestones down! For you to be there in a year, what goals do you need to hit each month to build towards the end of the year? Write the step down for each month. Finally, what habits do you need daily/ weekly to hit your Month 1 marker? Start there.