Everything I wish they'd told me about working for myself

It’s 2014 and I am sitting at my kitchen counter deciding to get rich.

I’m living in a student apartment, the kind of liminal space housing available to college students who want shuttles to campus and the right to keep pink wine in the fridge. Open in front of me is a laptop and a blank Rifle Paper Co. notebook with a floral pattern just misprinted enough to make it eligible for a stark employee discount. On screen a blonde woman is teaching, or maybe selling, but probably both.

She’s telling us the secrets, or so it seems. I furiously scribble down notes.

This is my first webinar, my first conscious trip down a sales funnel, my first time dipping a toe into the enormous waters of the online business industry. In the coming weeks I will doodle flow-charts in my stereotypically floral-themed notebook and copy sales emails into color-coded Google Docs, desperately trying to understand how everyone seems to be making so much money except for me. In the coming years I will have to reckon with the idea that I was sold a dream, a lifestyle—that I signed up, willingly, for a career full of both freedom and risk.

I don’t remember what that webinar was about, but I do remember how it made me feel: Like there was something I was missing, a source of information just out of reach that would make everything else make sense. Even now, a decade later, I can still access this feeling if I spend more than 10 minutes on the Instagram Explore Page.

I’ve been thinking a lot about that 20-year-old version of me as I get ready to recreate her experience for someone else at yet another free workshop of my own.

To put it plainly: Later today I’ll teach a class. After that class I’ll send emails inviting people to buy something. This is a sales funnel, a system that generates revenue for the business orchestrating it. In many ways, that makes me now the woman on the other side of the screen.

But for all of the studying and analyzing done by that girl sitting at her kitchen counter in Orlando, there are some lessons that can only be learned the hard way, from experience. What I’ve learned is that there is more to this job than copying-and-pasting someone else’s strategies. There are a million small decisions to be made, a lifetime’s worth of adjusting and editing the world around me to make space for dream to exist.

Below is my best attempt at offering you what I wish had been offered to me.

A very 2014 desk

Everything I Wish They’d Told Me About Working For Myself, But They Didn’t, So I Had To Figure It Out The Hard Way

1. You will care a lot, and that’s nice—it’s probably even a sign of alignment. But I won’t lie and say you won’t sometimes miss being able to watch a documentary or take a really great shower and not start writing a newsletter or workshop or video script in your head. Caring a lot is where the boundaries between work and life become particularly blurred. Maybe, despite what Nora said, it doesn’t have to all be copy.
   

2. Not everyone gets mega rich. Those people you’re seeing a) started early and b) are clearly really comfortable selling in the most effective way possible. It will probably take you a while to work through deconstructing, dissecting, and re-assembling the parts back together in a way that feels ethical and realistic for you. It may help to think of everything as an experiment—at least then you’ll be able to consciously decide what variables you want to test.
   

3. You will make the coolest friends. You’ll have someone to get coffee with all over the world. People will recognize you at concerts, which is weird but also pretty amazing? Try not to think about it too much at 2 am when you’re smoking a joint at a festival.
   

4. Librarians have a thing called “vocational awe.” The online business / social media / content creation industry has “aspirational labor.” Be mindful of how many I made a shitton of money and you can too posts you consume in a month. Selling the dream is an industry standard.
   

5. You will have to introduce yourself at house parties and happy hours. Figure out a description of your job that doesn’t turn you into a self-conscious squirrel. Downplaying your work doesn’t serve anyone. “I work in marketing” is a cop-out—say what you really mean. You never know who’s paying attention.
   

6. No one will really be able to hold you accountable except yourself—that’s the “self” employed part of the job. Be the kind of manager you actually want. Design the kind of office that works for you. No one is looking over your shoulder, so please release yourself from the idea that you have to be someone else’s definition of productive or impressive or successful. You’re better served by walking and doodling than toiling away at getting an inbox down to zero.
   

7. If you’re avoiding thinking about money in your life now, that will compound tenfold in your business. As above, so below. Do your taxes.
   

   1. As a matter of fact, all of that stuff you’ve got going on with people pleasing, codependency, overextending yourself and then stewing in frustration, low confidence, social anxiety—it’s all going to show up in these day to day tasks, too. How could it not? Sometimes your job will be to literally film yourself talking into thin air.
      
      Some people take this to mean that running a business heals you, but I see it more in the same way moving away from home at 17 shapes who you end up becoming. You’d probably be confronted with a lot of that stuff either way, but self-employment is a fast-track to revelation.
      

8. Most days you will wake up and decide what you want to do and then do it. Never stop being grateful for getting to live in that reality.
   

9. You don’t have to buy anything you can’t afford (see #7), but you do need help. The incredible thing is, you can build your own economy. Spend money with the businesses and people that you want to see thriving in the world around you, then introduce yourself. Those relationships matter more than you think.
   

10. Based on the desire you hold for your life—to write and read all day, get paid to make things, and spend a lot of time at the beach—the number one thing you will need is an email list. Not 10k on Instagram (I promise they’ll let everyone add links to Stories eventually), not whatever viral platform pops up next…email list. A platform you own and control, full of people who get it. Collect the virtual gold stars if you want, but remember what your endgame is.
    

11. The hardest thing to sell or buy will also be the most valuable: You need people you can talk to, candidly, about what’s going on inside your head. Don’t underestimate how much a small decision can shift your trajectory. Find people you trust to think out loud with you.
    

12. Being a contrarian is fine, good actually, until it becomes an excuse for not trying at all.
    

13. Every sale is a reflection of a relationship, every relationship is built on trust. They’re going to warn you about giving too much away for free—you’re right to question this principle. Helping is in your best interest. Just be mindful of what you’re receiving in exchange.
    

14. There is something only you will be able to offer. You probably can’t see what it is right now, and that’s okay. You’re still learning. Eventually you will realize that all of your rabbit holes, curiosities, side quests and interests add up into something. When this happens, follow the lede. Don’t pick a niche, trust that a through-line will emerge. Jobs was right that you can’t connect the dots looking forward, and I promise you will figure it out.
    

15. One day in the not-so-distant future, you will realize that there is a reason you always call out of work, procrastinate essays, and never seem to be able to “catch up” on laundry. Eventually you will accept that your brain is different, and that’s not just okay—it’s extraordinary. Best of all, it will become abundantly clear that your instincts way-back-when were exactly right.
    
    As it turns out, working for yourself is not just a fun idea or a path to millions, it’s something much more important: An accommodation. This career offers you way of living and being and creating in the world that you can adapt to the constraints present in your mind and body.
    
    You’re on the right track. From where I sit now, I am so grateful you’re trying. Keep going. We’re going to be okay.

Today: Join us at the Pretty Decent Internet Café for “WHY TRY? WHY YOU?” an Offer Design workshop helping you answer the two questions that change everything. Live 2/18 at 4 pm ET, recorded for posterity. Click here to RSVP.