Falling flat on my face.

My third full year working as a designer

by Darian Rosebrook
December 24, 2018

Year in review for 2018

I had decided to publish this draft that had been sitting here unfinished for an entire year. I wrote this last year, but felt that it wasn’t as helpful as I wanted it to be. I decided to hit post anyways to continue sharing my story of becoming a designer.

It has been three years since I started working as a designer in my spare time. While this has been an enjoyable venture for me, working in design as a side-gig has never been my intention. My goal was to have design be my main career from the get-go. This third year has been my most difficult.

For anyone who has made it past your first year or two as a designer, this post is for you.

Let me tell you all about how my plans for 2018 failed and what I learned while making the switch to becoming a full-time designer.

Also, I always want to be very candid with you. If you have questions or comments about anything I share, I am 100% up for starting a conversation with you. I can’t share everything from one year in a single post, or we’ll be here forever. ;)

For 2018, I had two goals

  • Switch to going full time as a designer by taking on client work

  • Finish and Launch the Compass of Design Community’s new membership site.

Let’s look back at where I started and where I’ve been.

  1. My first full year as a designer was hard for me (2016–2017), I had started learning design and deciding to leave my job as a bank teller and heavily research becoming a designer full-time.

  2. My second year was fun (2017–2018). I had opened the newsletter to the world and started building both the Compass of Design brand as well as my branding design practice, So Magnetic.

This third year has been a real stretch for me because while I expected to do great things in business, I had kind of fell flat on my face.

Hey, do you not have time for the full thing? Well, I respect that and here’s the high level of what I’ll be talking about (I do want you to know that these posts are usually full of resources that helped me get past those points):

What I learned

  1. Have a cushion in the bank before trying to rely on income from your business and make sure you keep it fueled so not to kill your business before it’s ready.

  2. Don’t try to do everything yourself. Find others who can compliment in areas where you need help.

  3. Spend less time trying to learn everything beforehand. Instead, learn through the art of making things and document your process.

  4. Find people ahead of you that you can plug into and learn from. As you continue to grow, curate who you follow to help you keep someone just a bit ahead of you in the spot.

  5. Rest. Your relationships require it.

Kill not the goose that lays the golden egg

I started focusing at the end of 2017 and wanted to put a plan to get both of my business models to turn a profit and support drawing an income from it to replace my day job.

With So Magnetic, I had a few great clients to launch myself toward this goal, Clinically Media and KeySpark. For me to make the switch to full time contracting work as a designer, my goal was to expand my reach and start taking on larger design engagements.

To be able to focus on these clients, my minimum level for client engagements would have to be more money than what I was making as a mortgage banker. Which was only less than $3,000 a month.

Because we had our second child this year, got married, and got a new apartment, any switch I did had to give me the certainty that we could support ourselves.

Why then am I telling you not to kill your golden goose? What happened?

I needed to make sure that whatever I was focusing on would give the most significant return in my business.

I had felt client work slowing down and so my focus shifted to building out the Compass of Design Community. When the clients started reaching out again, I was so focused on getting that finished that I turned down a lot of lower-tier clients.

Client work will always be the fastest way to make money as a solo designer. However, I felt I could make more of a difference by building out my web app.

What I should have done was use those smaller projects as portfolio pieces and still treated them with the same quality that I would have with a larger project. I’ve probably turned down 15 projects this year, effectively killing my golden goose.

If instead, I had tried to take on these small engagements, the projects would then live as examples to what I can do rather than having a giant unpolished web app. I’m correcting this now and putting a few projects in my portfolio before the end of the year, but this could have all been taken care of earlier and better set me up for success.

Talking to Sean McCabe, he likened what I’m making to building out a titanic on my own. I have something that is going to be huge, but I still have made a total number of 0 boats for the year.

What have I learned about revenue?

Don’t kill your main sources of revenue before it can either sustain itself or that you have a suitable replacement. Focus solely on the one thing instead having a few irons in different fires.

My business still requires a high-touch connection with clients, and it is not something I can simply leave and continue to have clients rolling in yet. I have nothing to share with Compass either if I don’t have more experience solving problems for clients.

Lunch is better with friends

I run a large community of designers that has grown to 90 people from all across the world. Yet, as I would participate and run that, I was still trying to do everything myself.

I have had so many of them reach out and offer to help me in some of the things I am struggling with, and my hard-headedness kept getting in the way.

I let some of them take on small areas of Compass while being able to manage and build out a bit of things from above, the whole project never got to go live in the iteration I intended. This was a huge learning point though in managing a creative team and after some time, I put a hold on any new work being done on this project. Without the income from either source, I had nothing to pay anyone for anything they volunteered for. It didn’t feel right to keep going, but it probably would have been finished had I stopped. It was a tough decision, but I decided to end production on the Community this year, to be picked up when I can actually dedicate time and stop focusing so much on trying to stay afloat financially.

Do, don’t think

I spent more time trying to learn what to do this year than actually implementing what I had learned. This lack of action can make a person feel very stale when actual work does come back.

I will say that there is a time to learn what you need to do, but it’s more important to do it.

Find a mentor

Investing in myself will probably always be a considerable expense for my business. This year alone I have spent nearly 75% of my (minimal amount of) earned revenue on courses, books, and personal mentorship.

Mentorship seems like it could be a daunting thing and very difficult to find, but know that people can be your mentor without you having to ask them.

Books can be the best way for someone to learn directly from a “mentor” even if you never reach out and ask them. I’ve consumed a few books, courses, and recorded talks by a handful of people, who I need to learn from, but are fairly out of reach for me to learn from directly. You can do this too by compiling lists of how and where to learn from content that are currently available and consuming that.


You may have a lot of energy now; I did at 23 when I started learning design. I treated this venture as if it were a full-time job on top of another full-time job. That was supposed to be temporary while I made my switch, but what was a simple change in schedule became a three-year habit.

I started going to be early, waking up early, and from when I had woken up until I had to leave for my job was the time I had available to do my design work.

I should have spent some more time resting, as this kind of schedule is completely unsustainable. I had rest days, but going as hard as I was, there has been very little to no recovery.

You have to have patience. It’s not going to get you anywhere if you start losing your health in the process.

Without rest from pushing at what you’re doing, you tend to start hurting the relationships around you.

Don’t get me wrong; you need to work hard to accomplish what you set out to do, but don’t work so hard that it starts affecting your health, and that you start to forget to live and enjoy the world around you.

My two business models?

  • Compass of Design, which focuses on delivering high-quality design resources to you; Right now Compass brings in just less than $130 a month. Most of the money for Compass is coming from the design book list which continues to expand.

  • So Magnetic, which is a small design agency that focuses on taking on client work and doing ad-hoc branding design. Client engagements have run from between $750 and $3,500, but with so few clients this year, there hasn’t been enough to sustain me full time, especially with the amount that I’ve invested back into the business.

It had been a rough year for both, and without proper time nor understanding on how to run either, the projects have remained just that, projects. I have a lot of things ramping up for the new year though, with one client in the books that will pay for the new year, and hopefully some more work after that.

I spent a lot of time this year entertaining larger inquiries with answers to linkedin messages regarding two large contracts that would benefit my business.

One of them is with a major airliner, which would put business revenue into the 6 figures for consulting work I already do. The other, though not as long, would give a significant boost to the amount of money earned for the start of the year. I’ve not successfully charged in the tens of thousands yet for consulting, but the work I’m doing, especially with the clients that I’ve worked with this year, will earn a lot off of the work I did for them.

People who made a significant impact this year.

As with every year, I want to specificially thank a handful of people who have made this year special. This does always end up being exclusive by nature, but know that if we had a conversation this year, I truly appreciate you, and everything you’ve helped me come to understand int he world of design.

I cherish good conversation, and I cherish those who’ve helped make a directly measurable impact in my business this year.

Shout out to these people for things, and I’m sorry if I forget to mention you:

  • Justin Jackson for all of the consulting and great educational content you’ve given me. I would give you all my money to download that brain’s worth of marketing and saas knowledge if I could haha.

  • Victoria Donovan for giving me a chance to prove what good consulting as a brand identity designer could look like.

  • Joe Busch for being willing to put up your skills for the Compass of Design work you’ve done. It’s been great getting to know you and your capabilities over the last few months. I appreciate you heavily.

  • Katie Wood for helping me think through all the ways not to manage people, if you know what I mean ;)

  • Chris Do, I’ve learned so much from you this year, I’m very proud to have taken your courses and learned asynchronously from you. Thank you for also including me in your live streams for critique. I’d probably keep my poster the way it was though ;)

  • Sean McCabe, you’ve been a huge inspiration for everything I’m trying to do. Thank you for all your honest feedback, and I really hope this next year really sails. Because it’ll be in part, a huge testament to your feedback on what I’m working on. Thanks again, friend!

  • To you, the dear reader. This year has been rough, but with all the distractions, I still want to focus on you and hope you get everything you need out of the Compass of Design to improve your skillset.

That’s a wrap for 2018, I hope you have a great rest of the year, and I hope you stick around for everything we have in store in 2019!

Originally published at https://compassofdesign.com on December 24th, 2018.