500 Days of Freelance

500 days into freelance. I didn’t plan on writing this but I’ve had a few things on my mind and read a few things and thought I’d share. These aren’t lessons. This is more of a status update and current state of mind. After 500 days of freelance I feel a lot of doubt and anxiety. I’ve had some terrible sleep too. I asked myself why? The gap between projects has been a bit longer than I’d like. This is my fault though. Aside from being picky, I’ve always relied on a steady stream of word of mouth and it’s worked out. I do have a few things in the pipeline but they can’t move as fast as I’d like. This is also new for me. I’m still used to working every single day at a company. I sometimes still type my old password into my computer. If we worked together you probably know the one.

I’ve been tempted to apply to a few full time roles too. Fantasized about collecting salaries that had been offered to me previously. That sweet sweet ACH honey dropping into my checking on the 15th and 30th. But the reason I want that is just distracting me from looking at the real problems I need to solve. This is also probably when most people would switch so I just need to find a way to stick it out.

Anyway here’s what I’m currently working on, won’t share the clients yet since its all pending and up in the air but they’re all generally in the fragile early stages of a deal:

Adobe Residency App (have barely started the app though and am unsure if I can submit a quality proposal while doing all this other work)
Client A - Content
Client B - Content Strategy
Client C - Content Strategy
Agency A - Content / Strategy
Agency B - Content Creation

To resolve anxiety around this I’ve made this week Biz Dev Week. My goal is to reach out to 100 people and brands. I’ve updated my website and resume several times in the last couple of weeks and gotten great feedback from friends. So thanks for that. Now it’s time to work on getting leads and sales. Mainly telling my story and communicating what I can and want to do and why I should be the person that does it especially to new people. I am not good at sales because I am essentially selling myself and that is a difficult thing for me to do.

In the book Atomic Habits there’s an example of a stockbroker Trent Dyrsmid who made brisk progress at his firm with a simple habit. He started each day with two jars on his desk, one empty and one with 120 paperclips. Once he arrived he’d start making sales calls, at the end he’d move the paper clip from the full jar to the empty jar and not stop until he moved them all. He quickly became the top sales person at the firm. This inspired me to adopt a modified practice for my business. I think reaching out to 100 people this week with personalized notes and questions should give me some results. I don’t have paperclips either but I’ll use X’s on my wall instead.

I’ve thought about where can I find projects? There’s probably a bunch of friends who may have something but I just need to ask. What’s the proper way? What if we haven’t spoken in a while? Is it weird to hit someone up and just say it. I thought all those things and sent out a text which never got a reply. Felt like dying after that but I’m still alive, so let’s try again.

Today I also made an account on AngelList. I’m not sure this is a good place for me but I want to exhaust all options. It seems okay so far. I’m also on WNW and updated my LinkedIn and probably should put some sort of call out on social asking for projects.

And lastly I realized I should look at industry news to see which companies and brands are doing interesting work. After making these adjustments I felt a huge weight lift. Now I know what tasks to do to find leads and generate business. My friend gave me great advice for cold emails too, the initial message is important but its also how you follow up. It can take 3-7 emails to get a person’s attention.

The next thing I’ve been thinking about is what kind of work I want to do and what kind of work I want to be known for. I don’t want to work with or for just anyone. This has limitations because the I’m still early in my career and I still need to make money to pay for a lot of things. This video from a Donald Glover interview in 2012 popped up on my timeline. There’s some gems in here but this is my favorite part.

It makes me sad that everybody wants to get noticed so bad, like everybody wants to get noticed and they don’t have enough like faith themselves to just be like oh let me just try and do something a littler different. Maybe I can do it, instead of like hopping on like… shit girls say yeah that [video] came out. Everybody like loved it and it’s funny and then everybody’s like “uhhhh Shit Black People Say, uhhhh Shit Puppies Say”

Like I don’t give a fuck about your shitty take on something

I’m not hugely famous but if I had gotten the fame I have now from making a shit girls say video, I’d shoot myself.

That would be worse than hell because it’s just like people would just like, I would always be living in fear cuz I’d be like what’s the next one of those of videos cuz I gotta be first because somebody else is just gonna be the guy who rips off this thing like it’s just like why, why live in this fear of that? 

It’s way braver to just take a risk and have people hate you for you. 

While I am trying to be intentional with my work, I also want to be open to experimenting and trying new things. And I’ve made a lot of shitty takes on other things. I don’t have my niche figured out yet. Which if you look at my previous year is pretty obvious. Standup, sketch comedy, creative strategy, brand consulting, social media management, photos, videos, joined a startup and a book. Where’s the focus? I’m okay with that. I know this is going to take time and I just need to think long term and figure out the small steps that’ll lead me there. But now I can ask myself before starting something. Is this what I want to be famous for? And keep doing?

It honestly does get pretty hard to stay on track though. Day to day can get pretty tiring or I’ll get so deep on a project I can only see 10 feet in front of me.

Which brings me to my next point, to counter this I’ve done two things:

  1. Put a written reminder on the wall of who I want to be

  2. I made a little folder on my phone with inspirational quotes, nice texts/DMs, and other things to look at when I feel anxious or unmotivated. I need to see that shit in front of me all the time because sometimes things get hard and I will forget why I’m in this game and I might quit. But this’ll help.

This system seems to work for me. Kendrick did something similar and had 5 Rules for himself. Bruce Lee wrote himself a contract, which he may have gotten from Napoleon Hill’s Think and Grow Rich based on the wording used.

The last thing I must do this week has been on my mind for a long time but I have not gotten around to doing it. I’m writing it now hoping it creates some accountability and urgency. I’m going to draw and write some personal thank you cards for each person that I’ve worked with last year. When they hired me they didn’t just give me money but validation that I can be on my own and I’m damn grateful for it.


[1] Even if I generate no new business this week I will at least get better at sales and my story.