Free At 50 Interview: Tom Werkman on Escaping the 9-5 to Become an Entrepreneur

Free At 50 Interview: Tom Werkman on Escaping the 9-5 to Become an Entrepreneur

Apr 09, 2021

Introduction to Tom Werkman of Werkman Outfitters and the Free At 50 Interview Series sharing dreams of becoming an entrepreneur.

I was just scrolling Facebook and came across an old classmate of mine from Holland Michigan. He’d posted this video asking if a guy can still dream at 51 and I stopped dead in my tracks.

It altered my entire day. I messaged Tom, who I hadn’t seen or spoken to in 30 years because I was utterly compelled to talk to him immediately about becoming an entrepreneur and his take on "dreaming at 51."

Not in a stalker kind of way (of course!) but in the way that you are driving this train down the track and people are looking at it thinking: is it possible? No more 9-5?

Maybe this gal is nuts for giving up the “paycheck life” and writing a blog well before “retirement” age. And then you find someone who gets it. And has a similar but COMPLETELY different story to tell. Same train, different track. Or same track different train.

Photo by Ben Kolde on Unsplash

Either way, Tom and I met up on Zoom within days and my plan to publish a series of interviews to share how it is possible to escape the 9-5 was born. And naturally I’m kicking off this series with my fellow WOHS (West Ottawa High School) alum and old, now new-again, friend Tom, who is headed full-force into his dream with his son Max.

Each interview will ask the same 8 questions to offer perspective on getting out of traditional corporate life. Enjoy!

Disclosure: As a blogger, I use affiliate links sometimes! I may receive commission from purchases I share, but it does not change your price.

1 Please tell us how, when, and why you decided to become an entrepreneur?

About 12 years ago I was going through a divorce and a good friend of mine at the time took me aside and said “You have a fresh start and need to stay in the land of the living. Don’t forget to say yes to people.”

Shortly after that, I was introduced to an individual that was a silent partner in an Orvis Endorsed Fly Fishing Lodge. They need some help with their bookwork. After some conversations and due diligence, I told them I’d be happy to help them, but I wanted to become a partner. So what my friend said to me was to “say yes,” I did.

My divorce started that path of taking more risk but not just any risk. I wanted to begin to figure out how I could make a living in the outdoor industry and the lodge was the path to achieving that dream.

Image by athree23 from Pixabay

2 What Inspired Werkman Outfitters to be your business of choice?

This is an easy question. My oldest son Max. About 5 years ago, both he and I were involved in a series of unfortunate events, both to my doing and not. Those events fractured not only my dream but his dream of making living in the outdoor industry as well.

Because my son and I own Werkman Outfitters together, it’s naturally the business of choice. He and I work very well together, learn from each another and challenge each other. You could also say we are each other’s alter ego.

Image by Arek Socha from Pixabay

3 Did you utilize on-line resources, courses, mentors, or coaches to build your business?

Yes. I have for the better part of my life been in banking and I still have that as a “day job.” For the majority of my career I was lucky enough to work for a small community bank that had an incredible leader and entrepreneur. I learned a lot while working for him. Not only about running a business but how to grow a business and how to take risks. The bank sold a number of years ago and he and I still stay in touch and talk about Werkman Outfitters. He still challenges me, gives me ideas to think about and helps me stay accountable to myself with what I want to do.

I also watch a lot of YouTube Channels, listen to Podcasts, and read. Some of my favorites are Ted-X, Ted Talk, human interest stories, etc. I do this mainly to help me keep focused on new ideas and how those ideas might relate to Werkman Outfitters.

Image by David Schwarzenberg from Pixabay

4 What has been most difficult in building a business?

For me, the most difficult thing in building a business has been facing my fear and taking the risk of at some point leaving comfort, the comfort of my “day” job. In order to help face this fear, my wife and I have agreed to a jump off-date. Until that time, we have made a plan and we are executing on that plan. We want to make sure we are as financially prepared as we can be for a steep reduction in my salary. If I don’t take this risk, I truly will never know what the limit of this business is and nor will I truly ever know freedom to live a life with purpose and leave a lasting legacy.

Image by Massimo Missaglia from Pixabay

5 How are you getting the word out about it / marketing Werkman Outfitters?

The way we get the word out / market Werkman Outfitters is through the main social media channels. It’s hard. We’re focused on building out our community and keeping our community engaged with us. In a highly competitive business like this, it takes a long time to build. I think we have a good story to tell though: a kid and his old man running a fishing outfitter together.

Image by athree23 from Pixabay

6 How has your life improved by being an entrepreneur?

For the first time, ever, I have alignment in my life. I can’t distinguish my work from my play and play from my work. I’m quite lucky that way.

7 Please share one book you’d recommend for our readers and why?

To be honest, I really don’t read but I watch a lot of YouTube. Some of the channels I follow are Ted Talks and Ted-X. These channels help me see the larger world and things in a different light or perspective.

Photo by Sincerely Media on Unsplash

8 What’s the biggest tip you would give someone wanting to start their own business?

If I can have two:

If you’re at my stage in life and are looking to transition out of the corporate world, make sure you have a plan. At my age, I’ve commitments that I need to unwind in order to make for a smoother transition, particularly financial.

The other piece of advice I’d give someone is, go easy on yourself as you transition. There will be highs and lows. Not only picture what your life will look like when you have left your corporate job but also what it will feel like. This feeling will help guide you through the lows and setbacks you’ll have as you transition.

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