In my blog post last week I mentioned that it seemed likely my full-time income beginning in February would be coming from Hermes (a match-making service for designers/developers looking for jobs in Chicago). As of yesterday, I'm a lot less certain about that. Actually... I'm almost entirely positive that it won't happen by February. And so I've found myself struggling to keep my head up, to keep looking forward.

I tend to suffer from excessive optimism, and I thrive off the excitement of future uncertainty. Even right now, as I write this with a knot in my stomach caused both by work and personal issues, I'm still optimistic about things to come. But the uncertainty of the next few months is driving me nuts. I know everything will work, somehow, at some point. I'll figure it all out. I always do. But it fucking sucks in the meantime.


Yesterday I found out that a fee I was expecting to receive for Hermes ended up falling apart at the last minute. Someone super talented, who's drastically under-utilized in his current job, was inches away from getting a great new job. Then, at the last minute, it didn't happen. The company's budget was no longer there to bring him on.

I don't know what to say except that I'm really, really fucking bummed. I wanted this guy to get the job so bad. He deserves it and I hate knowing he’s stuck at his current unfulfilling job a little bit longer. He'll find another great job, but it's going to take time. Hopefully I'll be there to help him out too.

Unfortunately, events like this cause me to question the viability of the entire project. Deep down I know I'm onto something really important, but it's difficult to keep my head in the game. Then, to top it all off, I'm also upset at the financial setback this caused. I was expecting a little over $7,000 from Hermes this month, which is no longer coming. There's another $5,000 that will hopefully be coming soon, but now I'm beginning to reassess my optimism about that too.

The fee I charge if you hire someone through Hermes is 10% of their starting salary. It's not a perfect pricing model, but it makes sense for the current state of the service. Typical fees for third-party recruiters are between 15-25%, so I came in on the low-end since my costs are a lot less. One hire can pay my salary for 1-2 months, and potentially even 3 if they're a senior engineer. However, situations like this, which are entirely out of my control, are where it breaks down and I question the whole thing.


Last year I lived off of a $40,000 income, so these fees would've allowed me to focus full-time on Hermes for 3 months. If I had 3 months, I'm confident I could help 10 more people get new jobs. More people in better jobs is the goal. The money is just the means for me to focus solely on this project while making my rent for a few months.

Instead, I’m back to freelancing through the end of February, if not longer. There’s a few more opportunities for Hermes to make enough money in the meantime, but I've found that it always seems to take a lot longer than I expect, expecially with something as difficult and senstive as hiring another human.

This is the part that's most painful... trying to juggle multiple priorities at the same time. How do I design and code this iPad app for my client while I'm thinking about the people who signed up for Hermes who need a job? How can I help this person find the best job when I'm neglecting my client, who's actually paying the bills? It's exhausting, and I'm really fucking tired.

Some days I'm tempted to get a job. I want a fucking paycheck that comes every two weeks. But more importantly, I want Hermes to fucking work. I'm sick of not making it, sick of not knowing if money is coming, sick of not helping enough people, sick of everything... but I'm mostly just sick of giving up. I've given up too many times on too numerous projects before. And finally here's one I believe in so deeply, and it's taking a lot longer than I expected.

Now I'm writing this publicly so I can't give up. I'm fucking tired and I need some support to keep going, but it's also a reminder to my future-self. I'll be stuck in this emotional ditch again. And when I am, I'll look back on this post and remember what it felt like. And how it got better. It always gets better.


If you're working on something and having a hard time seeing the future where it all works out... don't worry. Literally every single person who's ever created anything struggled with the same emotions. Talk it out with someone (or blog about it like me), and then get back to work. You'll do great.