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.

by Darian Rosebrook
December 07, 2017

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 your non-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:

  • design the logo and build a branding design system

  • build the site

  • design a branded email template

  • design branded title cards for the newsletters

  • build and design custom tools for the site to be used

  • create automation campaigns, sales funnels, and track analytics

  • branded products

  • social media profiles

In order to build So Magnetic I needed to:

  • learn to build a more professional process

  • learn to position myself with high value design clients

  • learn to price on value to the client rather than arbitrary rates

  • learn how to fit heavy hitting projects in my currently overloaded schedule

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:

  • What are the other people struggling with?

  • What types of designers are on this list?

  • Am I the only one who has problems with this?

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

I finally settled that for now my focus will be on companies that are working at transitioning from a small shop to something more serious and corporate.

This move will eventually require that I bring in help through subcontracting other freelancers and possibly even hiring employees to carry out heavy engagements.

I have to build iteratively, however, if I want this to work

The Services

Ideally we as So Magnetic will focus solely on branding but with extra services like

Branding Strategy

  • Strategy

  • Discovery and Research

  • User Experience

  • Brand Strategy and Archetecture

  • Positioning

  • Rollout Strategy

  • Brand Experience Strategy

Branding and Logo Design

  • Brand Development

  • Rebranding

  • Logo Design

  • Identity Systems

  • Brand Style and Message Guides

  • Print, web, and marketing collateral

  • Iconography

  • Web branding

  • Website Design

  • Social media branding

The Change in Professionalism

This year has been great for becoming a better professional.

I’ve spent much time this year auditing my professional process. If you want to learn more about that you can check out this post series on the client onboarding process

What have I learned?

Business is no joke. What I mean by that is that you can’t build a business lightly.

I’ve had to do plenty of things this year that I never thought about before hand during my first year of design.

Splitting my freelancing gig into two businesses (Design for Clients and Design Teaching for Designers) required a lot of business structure, accounting structure, and I’m still not sure if I’ll do my taxes right the first time.

I do plan on getting help with it this year, I just haven’t figured out where to go for that. I’m open to suggestions too!

Here’s a some of the highlights I’ve had from running Compass of Design and So Magnetic at the same time.

  • I rebranded the newsletter from “Designing with confidence” to “Compass of Design” back in February 2017.

The change came from not standing out in a crowd of newsletters. So I wanted to create something with a ring to it that accurately showed what this newsletter was. A compass to point people in the right direction when starting out in design.

  • I decided to focus solely on Branding Design for clients.

I was super short on free time because I still work 40hrs a week for a dayjob. I wanted to make sure that I had time for design work, so I picked the thing that I was excelling at and

  • I opened the Compass of Design Community in April 2017 and the group made it to almost 75 members by December

  • The Community Publication at read.compassofdesign.com follower count rose to 875 followers as of today, with my personal account driving nearly 1100.

  • 4 different community members also submitted an article to the publication with each getting great results from sharing there.

  • I’ve gotten a handful of offers for collaborations which I am still considering, but I’ve also had a handful of people offer to buy or combine Compass to turn it into their own thing.

I will never do that. Just so you know. My goal is to take care of you the best I can, and when the day comes that I’m no longer able to deliver the right content, the Compass of Design will shut down.

I’m not in this venture to sell or get bought out. I want to continue to deliver what you all need without the agenda of forcing what I want you to do or see.

Here’s some of the downsides that I’ve ran into

  • It’s very easy to run out of money if you aren’t getting consistent work.

  • With two businesses, I have had a lot of overhead to keep both going. I could double dip because of how my business structure is laid out, thankfully but still. Licenses, LLC Certificates, Insurance, Software, SaaS, supplies, resources, courses, all of these cost a pretty penny.

  • You can’t stop trolls from trying to ruin a good thing.

    I’ve had to remove people from the community this year, I’ve had to block people from social accounts, I’ve argued with people who challenged me on content (which wasn’t smart on my part)

  • Making a course is a lot of work, so much so that I had to put that on hold until 2018 while I get my businesses stable (I know what I have planned will be worth it to designers though, expect to hear about that at the turn of 2018)

  • I had nearly 700 people go through the self assessment tool, which is still very unhelpful. I want to make it better, but it’ll be difficult to tell people I fixed it so they can try again.

I never asked for any info in order to send them updates. I just didn’t have time and had to leave it there as is.

  • I’ve had a serious lack of clients while building Compass due to time restraints. But thankfully that means I’ve had more time to audit and reflect on my process with the 6 that I’ve had this year.

I’ve also had a lot to learn from individuals that I’ve met around building both companies.

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 things I’ve learned)

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 — 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 — [Matt Bertino]() Your insight and building ofMail Snail has been great to see what iterative changes and perseverance can do with incoming revenue.

Dan Coverdale — [@dtcoverdale](http://Twitter.com/dtcoverdale) 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 — @SaraSaysData Even though our interactions were brief, I’ve learned a lot from what you’ve shared this year about data visualization and got to use things I’ve seen you share for reference material. Data visualization is an interesting thing and has great ethical and moral impacts.

Dan Pererra and Amy Parker Dan Perrera 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 and I appreciate the support with shots I post to Dribbble

Jonathan FriesenJon 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. It’s been great hearing how working with clients and gaining interest for saas products works. I gotta step up my dev game.

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 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. You have a great amount of insight when it comes to design jobs and that’s an area I might ask more about in the future.

Sean McCabe — [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 — [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.

I’ve learned that you have to make writing much easier to digest.

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

UX design is something that everything needs and should be used to make anything better.

Tyrel ChambersTyrel 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.

You helped me test out the process and taught me that running a huge team is hard, but with persistence you can get a lot done.

Juliane Bone — 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.

So the more you challenge yourself to get better as a professional, you challenge me to get better too.

Skip Jones — 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 OsorioManuel 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 Morris Steve! Your comments on Dribbble have always been good motivation to keep going. I’m always impressed with your line work, and you have an aesthetic down that’s 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 — 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 — 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 — 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 — 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 — 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 — 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 —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.

Aaron BookerAaron Booker It’s awesome watching you starting these challenges, if you keep these things up, you might actually give me a good run for my money. You’ve got a great eye for UI and I’m looking forward to seeing what you got. (:

Joe Busch — 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@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 — Akna Márquez 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:

  • Getting my case studies onto my website

  • Leveraging referrals and outbound marketing efforts as well as inbound marketing efforts

  • Building up a cash reserve that equates to 6 or more months of all expenses at my current lifestyle level

  • Building up a cash flow to sustain that cash reserve or blow it to bigger proportions

  • Pricing on value rather than time or flat fee (that means not over charging my clients, and not undercharging myself)

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:

  • Sending out free stuff like stickers, pins, and digital goods to the members of the community (still deciding on semi-annually or quarterly.) Just like this pack going out in January.

  • Finishing the Designer’s Self Assessment Tool’s second version to include a much better learning path that is custom tailored to a person’s level of experience and chosen design discipline

  • Start doing more things like live events and group challenges

  • Explore what the platform can become and start the vision of what version 2.0 of the community looks like and how to grandfather what ever group exists into that new version

  • Continue to do the things that drive the most value to members of the audience

  • Make many new friends

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.

As a designer, have you got your skills ready for next year in 2018?