How I Shifted My Career From Footwear Designer To A Successful Graphic Designer

from Framingham, Massachusetts, USA
started August 2020
alexa rank
market size
avg revenue (monthly)
starting costs
gross margin
time to build
7 months
growth channels
Word of mouth
business model
best tools
Adobe Suite, Instagram, Facebook
time investment
Full time
pros & cons
39 Pros & Cons
1 Tips
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Hello again! Remind us who you are and what business you started.

I’m Darin Hager and for most of the past 15 years, I’ve been a footwear design consultant and owner at fitness sneaker brand, Heyday Footwear. After a 12 year run, I walked away from Heyday in 2019 after being unable to raise the capital needed to scale. I took the shutdown of Heyday pretty hard; it felt similar to the grief over losing a loved one.

While I’ve had a few freelance footwear projects, for most of 2019 I gigged as an Uber driver. While that helped me a tiny bit financially, it helped more (initially) by giving me something to do. After 6 months I started to question if I would ever be able to find a “real job” ever or would driving be my career?

I’ve been a footwear designer for 20+ years and am pretty sure I was “aged out” of a corporate design job, due to running my own consulting agency and brand for so long, my age (49), and what employers perceived to be my desired salary at this stage in my career.

Even though I didn’t seem to be in e-commerce any longer, I still kept up on the several Shopify Entrepreneurs groups I was so active in during my Heyday. When I was active, I used to see a lot of great posts by Uri Weinberger. In the Spring of 2020, we ran across each other in a Tesla Model 3 group and it was a few weeks later in July that I saw Uri had posted on LinkedIn for an email marketing manager/head designer. I read the description and had an epiphany; “I know Klaviyo, I know Shopify and I’m a designer. I think I can do this!” Since Uri and I knew each other from FB, it was basically a warm introduction and I pulled out all the stops to get that opportunity.

A little detail that helped push me over the finish line while interviewing was the email campaign I created in Klaviyo with me as the subject matter and “Hire Darin” as the CTA. I wanted to show that even though my extensive design background was not specifically email focussed, I could create right out of the gate with little to no supervision as a 100% remote worker in a 100% remote agency and that I go the extra mile. That mentality was honed over 15 years as an entrepreneur and brand owner. Of course, always the designer, I cringe when I compare it to the work I create now.

Six months into it and I’m loving this role! I have 4-8 clients at a time, from fitness and wellness brands to a national coffee roaster, CrossFit apparel brand, and a big E-bike brand. One of my favorite brands to work with is Violate the Dress Code, a fitness brand that I had done work with at Heyday Footwear. Founder Chris Zimmerman and I have been good friends for 6 years. I’m always pumped to craft their email designs and strategy every week as it was the same category and audience as Heyday.

I’m thankful to have this career change after feeling like my career was lost at sea after Heyday. I’m especially thankful to have a job I love during this tough time.


Tell us about what you’ve been up to! Has the business been growing?

The email portion of Adjust Media’s business has grown from 2 brands to 8 in six months; all of them 7-8 figure brands. I craft email campaigns, both the flows, opt-ins, and strategy aligned with the ad campaigns handled by a few of our colleagues, spread throughout Canada. I also design Facebook ads for some of our clients who aren’t on our email package.



Despite the toll Covid has taken on the world, e-comm has continued to flourish and our clients are reaping the benefits of such a captive audience.

One strategy I like to employ with our apparel brands is to create segments by size (or color) and send highly targeted campaigns to segments by size. This works especially well when a brand has hash or mixed sizes. For example, if there are only size Medium leggings available, I send to the segment of Bought Medium or Viewed Medium only. This has worked extremely well for us.

What have been your biggest lessons learned in the last year?

2020 was a huge year for me; I went from thoroughly disgusted and depressed about my career choices in January to enthusiastically kicking ass in my new role by September.

What’s in the plans for the upcoming year, and the next 5 years?

I plan to continue to learn new techniques in graphic design, copywriting, and strategy while delivering awesome performance and transparency to my coworkers and clients.

Have you read any good books in the last year?

The Freakonomics podcast (and books) have always been a favorite of mine. I love to find out the hidden side of everything.

Advice for other entrepreneurs who might be struggling to grow their business?

Be steadfast in your commitment to success and nimble AF in your approach to getting there.

Are you looking to hire for certain positions right now?

I hope we will be later this year but we shall see!

Where can we go to learn more?

If you have any questions or comments, drop a comment below!

Darin Hager,   Founder of Hager.Design
Pat Walls,  Founder of Starter Story

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