We were lucky to catch up with Amanda Keller recently and have shared our conversation below.

Amanda, appreciate you joining us today. If you could go back in time do you wish you had started your business sooner or later?

It’s easy to say I wish I had started sooner, but I also trust in the universe’s timing.

I left my corporate job in January 2024, after nearly 13 years with the same company. I spent my entire career with this organization and was very attached to it, but in 2019, I started to feel unsettled. And eventually, I admitted to myself that I was ready to move on.

In fact, I was sitting in a recruiter’s office the day before the pandemic shut the world down in March 2020. That was the universe telling me to have a seat. I started freelancing consistently, and eventually my side hustle was fueling me while my full-time job drained me.

In October 2021, I had had enough and was ready to go all-in on my own business. But then me and my husband found our dream home, and I couldn’t give up my salary. That was the universe telling me, “Not yet.”

In November 2022, I thought I had my mind made up that I was ready to leave. But there were significant changes in the organization, which I saw as my destined path and invitation to achieve my long-awaited career goals. That was the universe telling me to be patient.

Finally, at the end of 2023, I had the nudge I needed to take the leap. I essentially gave a 5-month notice, and they graciously gave me the time to prepare to switch from full-time employee to full-time entrepreneur. I spent my holiday break launching my rebrand, and my first day back to the office — coming down from this exciting milestone in my business — I took 15 minutes trying to convince myself to get out of the car. I had just spent months building something I was SO excited about, and ready to share with the world… Why was I going to put that on hold for another three months?!

So by 9am that morning, I officially resigned and moved up my departure date to the end of that month. Sunsetted that chapter of my life was special and celebratory and came with more ease than I ever anticipated. I’ll forever be grateful for my time there, and carry with me all the invaluable lessons.

My first year on my own has been nothing short of amazing. I’ve learned so much, I’ve stayed steadily busy, and have gotten to help more than 30 business owners. So yes, based on the first 12 months I wish I had started sooner, but I also believe timing is everything. I went all-in on my business and said “HECK YES” to entrepreneurship exactly when I was meant to!

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I was failing Accounting my senior year of high school — which in hindsight isn’t that big of surprise. As hard as I tried the “get it”, I decided to drop the class at semester and picked up the one art class I wasn’t already taking — a digital arts course in which I learned Photoshop.

At the time, I never could have seen how important that decision and change in trajectory would be for my future. After high school, I had no idea what I wanted to do, but like many 18 year olds, I figured I should go to college so that I could eventually get a high-paying job.

For some reason, I landed on Dental Hygiene, but at the very last minute (literally, like the Friday before the Fall semester started) I signed up for the Graphic Communications program at a local technical college. I learned more about Photoshop, and was introduced to QuarkXPress, InDesign, and Illustrator. I was taught color theory, typography, image manipulation, print design practices, and more.

While I was in my last month of school, I met someone who eventually referred me to a local job. I was working for a medical billing company at the time, and although they were generously flexible with my class schedule, I thought this new opportunity could be a chance to get my foot in the door and some experience for my resumé.

Little did I know, I would stay there for almost 13 years and it would change my life forever. It significantly inspired the business owner I am today. In fact, it’s where my entrepreneurial spark was ignited. It’s where I honed my design skills and learned how to be a copywriter, digital marketer, and leader. This on-the-job, in-the-wild, real-world experience was the best education I could have ever asked for, and I got more out of it than I ever would having going into debt at a four-year university!

It was a roller-coaster ride of highs and lows, and I loved it — even though there were many hard seasons. It transformed me into the person I am now, and I’m endlessly grateful for my unique journey.

Today, I work with service providers of all kinds. I’ve built brands and websites for authors, contractors, spiritual healers, bars and restaurants, therapists, athletic trainers, even a dog poop clean-up service!

I strive to eliminate the frustrations of DIY and dud designers of the past. All too often clients come to me still feeling burned from previous experiences. I consider it a privilege to be able to heal those wounds and change their perspective.

I deliver marketing-fueled websites, strategy-driven visual brand identities, persuasive copy and compelling messaging, and emotive photography.

I don’t really have a “design style” because from logos to websites, I design for my clients’ customers. I design to express their personality, the desirability and quality of their services, and to tell their unique story — that draw in their target audience like a lost captain to a lighthouse! Through my empathetic nature, I’m easily able to step into their shoes and feel what they feel, and in turn, create solutions that solve their deep-seated pain points.

What’s a lesson you had to unlearn and what’s the backstory?

In order to become an entrepreneur and operate the many moving parts of my own business, I had to shed a lot of the old stories I believed about myself. Most of which came from my years in corporate.

I think the hardest one was that who I am at my core was the wrong way to be. Meaning, that the soft parts that make me who I am — my empathy, my compassion, and leading & creating from my heart — were going to hold me back.

I worked in a very masculine business and industry. I felt in order to be successful or to be taken seriously, I had to turn off the things I considered to be my best characteristics. The things that make me, ME. When I tried to show up as someone I’m not, it drained me beyond belief, and everyone around me saw right through it.

I also lost myself in the job. I gave it all the credit for the best parts of my life. Looking back, I can see now that is was my decisions, my resilience, my work ethic, my critical thinking, and my willingness to answer when opportunity knocked that got me to where I am today. It may have been the door, but I was the one who walked through it!

Another big theme in this same vein is unlearning that there’s always a right or best way to do something. Believing this has driven me directly into a comparison trap, making feel less than. Like I’m not good enough to do this work. That I’m not qualified or smart enough. In the past, this has paralyzed me and sent me into scarcity spiral. And it takes a lot of mental effort to bring myself back out of it — mental energy that is better used elsewhere, like solving problems for my clients!

Is there something you think non-creatives will struggle to understand about your journey as a creative? Maybe you can provide some insight – you never know who might benefit from the enlightenment.

The creative journey is fluid. The spark isn’t always just “on” or easily accessible. For me, it ebbs and flows, and is influenced by everything from my routine to the seasons to the task at hand.

Also, there are many different paths to the same outcomes. Every designer is going to have their own unique methods or approach or prefer different tools. I don’t like how it feels when I see other designers on social media who speak very aggressively and definitely (and judgmentally), so I try my hardest not to do that to others. Especially my clients. I never want anyone to feel stupid for not knowing something or doing something differently than me.

And I think the harshest truth is this: You get what you pay for. Too often, I think people assume design is easy, and that we can just “whip something up” with little effort.

When hiring a designer, you’re not just paying for an end product, you’re paying for the VALUE it provides and what it can return to you. You’re paying for years and years of experience, education, growth, trial and error. You’re paying to tap into their heart and soul — because it’s art, it’s personal! And when you have someone like me who takes their skill development seriously, can deliver meaningful results and evolution for your business, and is going to care about your brand like it’s their own — it’s beyond worth the investment!

Contact Info:

• Website: https://www.northwoodscreates.com
• Instagram: @northwoods.creates
• Facebook: https://www.facebook.com/profile.php?id=61553977138095
• Linkedin: https://linkedin.com/in/amanda-keller-northwoods/

Image Credits

Jess Burns
@thelovelyoak