I just completed two years of moonlighting as a freelance designer.
Thu, Dec 07, 17
21 minute read

I just completed two years of moonlighting as a freelance designer.

Here’s what building two design focused businesses at the same time looks like. Two years ago in this first week of December, I started learning to code websites. I had my eyes set on becoming a freelance web designer. The glam and glory was appealing, meaning that I was able to do something that interested me (finally) and get paid handsomely to do so.

Originally posted on Compass of Design Original article link

Darian Rosebrook's avatar— by Darian Rosebrook

And what building two design focused businesses at the same time looks like.

Two years ago in this first week of December, I started learning to code websites. I had my eyes set on becoming a freelance web designer.

The glam and glory was appealing, meaning that I was able to do something that interested me (finally) and get paid handsomely to do so.

This path has set me on one of the best and trying journeys of my life. Along the way I have met new and interesting people. I’ve failed at a handful of things that opened it’s way to new things or trying again from different angles.

I’ve built and perfected processes that make building two businesses at the same time less stressful than it was starting out.

That story has been told in my first year’s year-end review, geared towards helping new people to the web design industry.

2017 was a good year

But it was the most challenging of them all

I have been able to accomplish so much, yet not enough. It’s felt fulfilling, yet severely lacking. And I’ve been growing a lot, all while standing still. I’ve been making money as a designer, but I’m not quite where I need to be to sustain all this.

Let’s talk.

This year started out great too.

I had a long sit down at the end of 2016 after spending nearly all of my free time working months on the redesign of an enormous web app as the only designer on the project.

This project left me with time in order to focus on continuing my learning of design, no time to build my business on the side while working with KeySpark and my full time job, no time for my family.

And I had to really consider if now was the right time for me to become a web designer.

When you are trying to build your business on the side of having 2 day jobs (A bank teller and a web designer for a remote dev agency) you start to have scope creep, but for your obligations in life.

If I were to survive, I would need to focus.

That was this year. Focus.

After a sit down talk with a friend who had been a designer for years before starting her family, she had mentioned to me that there are more things to design than just websites.

She had me audit what I was doing, where I was spending most of my time, where my heart was at with everything, and then imagine myself if I went that direction for the next 15–20 years.

Was that line of work going to satisfy my urge to create? Could I keep up with the rapid growth and iteration of the design world? What if what I’m good at designing isn’t hot anymore? Do I have the ability to change? Do I have the skills right now to be creating timeless designs?

These hard questions got me to audit what I was doing and what my true goals were with being a designer.

The Plan

It’s like I had suddenly started to see what I wanted to do in life. It’s a really weird and fulfilling thing when you have the pieces of what you do and who you’re best equipped to help cross each other.

I had two goals

  1. Improve my professional process to move into the premium market of designers, building out the foundation to start a branding design agency focused on helping businesses transition from a small mom-and-pop into something more professional or corporate.
  2. Build a platform to help designers who can’t afford design school (or want to teach themselves) learn how to effectively build their skills, market themselves better, becoming a better professional in the process.

The Coach

Back in December of 2016, my friend Justin Jackson had been opening up slots in his mentorship coaching group he was starting. This group was a run of four months of personalized coaching, goal setting, group Q&A events, and progress checking.

This kickstarted my year with some heavy goals and ambitions that I knew I had the ability to finish. But Justin, seeing what I planned to do, knew that I would be burning myself out if I hadn’t fixed my current work situation.

I was exhausted all the time, working my butt off for a ~$17,500 take home income along with working a second job that was barely paying anything better than that.

If I was going to be focusing on growing my business, I had to make sure my day job income was taking care of my base costs.

Had I relied on my side income to pay bills, I would have damaged my passion to do this venture.

Your side-hustle, when starting out, is like a sapling. If you try to lean up against it, it’s going to snap like a twig and become crushed.

When you have the business where it can support your current lifestyle without the use of you business income, along with a solid foundation (months of income saved in the bank) and a steady stream to nurture it, you are able to leave the day job.

I was currently using too much of that side income and needed to cut to bare necessities and focus on increasing my income on both fronts.

Great minds think better together

After the coaching started, we formed an online mastermind meetup where the people who were in the coaching sessions would meetup on a video hangout every week to share progress and gain feedback on our projects.

The people in the group were mainly developers who each had some sort of SaaS Product (software as a service) or product they were selling.

Our goals this year was to make a sustainable living on the things we love to do, and build out new ideas to test.

As I was working on all the things that resulted from my coaching sessions with Justin, this group was a way to keep myself more accountable to the goals, along side that I was paying a lot of money in order to have access to the things I was doing.

The advice and feedback from both sides of this coin (Mentorship and Mastermind) was exactly what I needed to give me the motivation to build out and test the feasibility of my ideas and fed each other into what naturally happened.

My design business split into two sides of the same coin

These businesses feed each other.

One of them does branding design engagements with clients

The other shares the experiences, knowledge, and fosters growth around becoming a more professional designer.

How do they feed into each other?

In order to build Compass of design, I had to:

In order to build So Magnetic I needed to:

Rebranding the newsletter

You have a lot of thoughts, ideas, and experiences locked inside of your head and most of them will die with you.

— Sean McCabe

This newsletter isn’t something that I wanted to do solely for myself. Plenty of people could benefit hearing from someone who is in the fight, working on creating a design business from the ground up, learning about design along the way and then turning around and teaching what he’s learned.

The path to becoming a designer is also very hazy and not well documented outside of the college/design school setting.

I wanted to be able to be a guide to show these people who are eager to learn, but lost without an idea of where to go. I wanted to create the compass that guides them.

This turned into changing my focus on writing about Designing with Confidence, to me helping people find the direction they needed to go to level up their design skills.

(Yeah the newsletter was originally called Designing with Confidence)

In order for me to teach design to others, I had to become a perpetual design student.

There will always be something to add on a topic, because even if someone else has written about it, done a talk on it, created that theory before, there’s no new ideas out in the world any more. Just a fresh perspective.

I would say that running my design newsletter has been the quickest and most efficient way for me to learn design.

As the newsletter grew, so did the position of the brand. Ideally, the brand is a way to help empower other designers with the skills they need to defeat impostor syndrome and start designing with confidence.

New things were added every week to this brand until it became it’s own full standalone thing, all seated within it’s parent brand** So Magnetic.**

The Compass of Design

At a certain point, I had several people who were on the newsletter that had started asking questions about the other people on the newsletter.

Questions like:

These questions had got me thinking that I was hitting close to the right spot with the positioning of my newsletter. But someone can only get so far on the thoughts and insight of one person.

So I decided in April to open up the newsletter list and start a private slack community for the people who signed up for the newsletter.

The Community

The group started growing very slowly for the first few months.

Originally I was sending invites to anyone who joined the newsletter. The amount of accepted invites compared to the actual signups were about 1 signup to every 4 or 5 that joined the newsletter.

At a certain point (and I can’t remember when) I added a little checkbox that said “also, send me a Compass of Design Community invite” which worked better so that I was only sending invites to those who wanted it.

But then again that only worked a little bit better.
By the time we got to 50 people in the community, I had started dealing with a few really negative people that made it into the community.

This was a group I built to foster growth and I ended up having to talk to a few members individually, I had to kick one person out of the group, another left of his own accord.

And that got me thinking of the value that you get being for being a community member. This thing is meant to help foster the growth of your skills and help you become a better designer overall faster. All while building friendships, acquaintances, skills, getting valuable feedback on work you’re doing.

I decided to close open registration for the community back in August, and new members were only added if they messaged me personally asking to get in.

I did something soon after. I started charging new members for community membership. This did 2 things.

  1. Something that is open to everyone is open to both the good and the bad people. By charging for community membership, I was able to help improve the quality by challenging people to be serious about wanting to become a better designer.
  2. The increase in income from membership helps me focus exclusively on helping these people grow and continue to invest back into them. Makes me want to invest things like giving free goods, free course material, all sorts of stuff. It improves the quality of the community membership on both fronts.

As of this article, the community has grown to almost 75 people. All of you in there are founding members of something great to come. I hope you all continue to participate and grow together over the next year.

The Products

Products like the design resources will continue to be added as they come available. I plan on finishing the other two on the list soon and I hope to continue to add as many resources as people need.

The Coaching

I have plans for two courses.

  1. Marketing yourself as a designer (50% built out)
  2. Designing with Confidence: The founding principles of design (25% built)

I also plan on expanding on a few of the topics of 2017 in video form on YouTube.

I’ll open up myself for private mentoring and coaching sessions through my personal site where people can sign up to get specific and specially tailored feedback and goals directly from me.

I plan on trying to get some small gigs teaching what I know in workshops both online and in person.

There is so much in store for the Compass of Design and community as the brand continues to grow. You’ll see my goals at the end of the post.

Rebranding my design business

This meant that along with changing the position of my design newsletter, in order to reach a higher market of design clients, I had to increase my professionalism.

Positioning was key, so in order to level up with my design business, I had to start reverse engineering what a successful branding agency has.

Qualities of an agency afloat

  1. Excellent communication skills between the client and designer
  2. A higher level of design skills than where I am right now.
  3. The ability to uncover goals, expectations and price based on goals and expected value of the project
  4. The ability to employ design strategy through a consistent professional process
  5. Being selective with taking on clients
  6. Extreme confidence and backing of choices made
  7. A large body of work that compliments and assures clients they’re making the right choice
  8. Effective case studies that entice, explain, and convert visitors to start new projects
  9. A clear and direct niche
  10. An excellent brand positioning statement

I am nowhere near finishing all of the things on this list. But, with what I have completed, I have become a much better designer and business person through it.

I’ve been doing what I can to position my brand here in a niche market

But even then it’s insanely hard to pick a positioning statement. So why not use all of them?

Yeah that hasn’t been quite as effective as I would have liked it to be. haha

The Target Market

The Services

The Change in Professionalism

This year has been great for becoming a better professional.

The Process

What have I learned?

Special thanks, in no particular order:

(and this is not a complete list, I promise there’s so much more I’ve learned form each of you. These are just some of the biggest)

Sara Weishaar — For giving me grace and patience as I continue to build this for us these next few years. You, my beautiful fiance, and our beautiful children continue to inspire me to be a better man to support you all. I love you and do this for you first and foremost. Even if sometimes you’re frustrated that I’m working a lot, that ends soon and we’ll put these past few trying years behind us. I love you.

Justin Jackson — for kicking my ass into gear this year to build things and consistently auditing where I’m at and where I need to go in order to bridge that gap. (MegaMaker, JustinJackson.ca, MegaMaker Club)

**Matt Bertino **— Your insight and building of Mail Snail has been great to see what iterative changes and perseverance can do with incoming revenue

**Dan Coverdale **— For helping me understand the joys an follies of designing products as a business (especially across the pond). Your neo-retro aesthetic is always refreshing to see.

Mike Eppel — I don’t think I ever want to try to make a plugin at all anymore. :P

**Michael Newman **— Thank you for all your insight with helping shape my ideas to build out Compass of Design.

Sara Wood — Even though our interactions were brief, I’ve learned a lot from what you’ve shared this year

**Dan Pererra and Amy Parker **— Our small comments back and forth around your project of visualizing the Red Sox Scores has been an interesting way to learn about abstract data visualization

Jonathan Friesen—You were the first person to buy a product from me this year. Thanks! Also, your adventures with projects, travel, and tenacity in life have been really inspiring.

Jordan Faux — My friend that inspired me to become a designer and learn illustrator. Though I might have outrun you initially, I’m always there to help you get caught right back up.

**Michael Weibel **— Michael finished the 100 Daily UI challenge this year. Every piece he’s shared on Dribbble and twitter has been epic and it’s been great seeing someone’s skills build incrementally over time. If you’re ever state-side, you have a friend here in Washington State! Maybe some day I’ll make it over there too.

**Emily Ellis **— Thank you for being a part of the community. I’ve learned a bit this year helping answer questions and giving feedback on your work.

Sean McCabe **— I’ve been in the **seanwes community since March 2016, and I have yet to be disappointed by the access to valuable, quality content he and his team produces. It’s a standard set for what I plan on putting out in the world for Compass of Design. Very much appreciated.

**Kyle Adams **— You helped me become a better writer this year, find the best process on picking colors for design to date, and continue to inspire and support my work. Thank you.

**Joelene Weeks **— It’s been great getting to know you. You and I have a lot of parallels when we talk. I would hope to continue helping you grow with UX design and help you while you build out your portfolio. (:

Tyrel Chambers — Thanks for the opportunity to work with KeySpark this year and help me perfect my client process for So Magnetic. Your continued support and friendship has been one of the most valuable things to me.

Juliane Bone — You have such a brilliant mind when it comes to branding solutions. I’m always impressed too by your work and voracious appetite to learn about becoming a great branding expert. You inspire me to grow each time with those great questions you ask.

Skip Jones — You were one of the first 5 people that started the Compass of Design community. I appreciate all the support and the resources that you’ve given that helped shape my venture here.

Manuel Osorio — I’m always interested in the projects you are working on in your education classes. I’m glad that a lot of what I shared with Compass that you’ve been able to apply so much!

Ross Litzenberger — Ross, you’ve been a tremendous help and valuable friend when it comes to having questions about Git, RoR and just being a good friend, and texting me to check in. I think you’re the only one who does and I always appreciate that.

Steve Morris — Steve! Your comments on Dribbble have always been good motivation to keep going. I’m always impressed with your line work, you have an aesthetic that is simple, but difficult to do right. I think you’ve been really growing your skills this year and I’m looking forward to seeing how you grow next year.

Amy Kotas — Thank you for all your insights with running a side business with a family. Sometimes just seeing you hustle as hard as I do has been enough to help me keep this up. Thank you.

Ben Kochavy — I’ve ran into so many people you’ve associated with this year that I’m beginning to think we should become better friends. lol

Katie Wood — Thanks for challenging me to think of things within the community and constantly sharing good design resources. I hope that you continue to grow your skills with design and your Heart & Sola Venture (:

Peter D. Kaizer — I don’t know of anyone who’s shared my articles more than you. Thank you, friend. Your support is appreciated and know that I’m always here to answer questions should you have them.

Andrew Krause — Also among the first 5 of the community members and a friend. You build things so quickly that I get jealous sometimes and motivated to find better ways to automate things. You got an interesting brain.

Spencer Fry — I’ve had a lot of fun getting to know you and the things you’re excited for to help your community with Podia. As a customer, I appreciate your human interaction and level of support. I aspire to have the dedication you have to your audience. Thanks for all the support (customer and personal)!

Brian Hollingsworth — I get to see someone who’s a few steps ahead of me building his design practice in real time. I’ve taken many notes on the things you do and share and I must say that you inspire me to be more vocal about how branding and design impacts business.

Joe Busch — You’ve got such an interesting future ahead of you. I hope you get a lot out of being around other designers this year, and I look forward to seeing your work grow. You’ve got the talent, now let’s build those skills.

Jonathan Holt — Youv’e liked nearly every single Dribbble shot I’ve put out and you’re not a bot. So that got a mention.

Akna Marquez — I get inspired by anybody who does a different field of design than I do. Reading your articles and being on your newsletter help me understand more about design from angles I never thought about. The conversations we’ve had were insightful and glad to know that we’re all working on figuring out where we want to be with clients.

**Rogie King and Justin Mezzell **— I made pins and stickers for the community and it’s inspired by the fact that you guys work so hard to put out quality crap. I want to put out quality crap like you guys. Keep jiving!

**Meg Robichaud, Meg Lewis and Laura Bohill, Helen Tran, Dina Rodriguez, Deidre Olsen **— All of these people have helped me understand a lot of what women deal with. It’s been insightful and helped me think of how I act as a man and audit myself for how, when, and what to do to help women be uplifted instead of hindered in society. Thank you.

If you’re reading this and weren’t mentioned, don’t think I don’t care about you. These are some of the biggest things I’ve learned this year (and can remember right now as I’m building this article) If you and I have interacted at all in the last year, know that I appreciate you and you are worth a lot to me. Don’t for a second think that I discount you or our interactions (:

My vision for next year

For next year, I want to be able to finally retire the dayjob.

Anyone who does know me knows that I usually go to bed around 10 or 11pm and wake up around 4 am to get working on my design business.

That has to stop. I can only do this for so long until my body gives out.

Next year I plan on 10x-ing my design business

This will mean:

Next year I plan on 10x-ing the value behind Compass of Design Community

Membership making it a better investment for new members (and current ones)

This will mean:

I am so excited for where this is going. I hope that you’ll all come with me and work on your projects like I am.

I want to thank you for everything you as an audience has given me in support. Without it, this would be a very dull adventure.

Originally posted on Compass of Design on Dec 07, 2017

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