How This Chief Carriers Driver Went From Programming to Driving Flatbeds

December 16, 2021
driving flatbeds

Learn how this Chief Carriers driver went from computer programming to construction and now to driving flatbeds. 

Don Wilkes III just celebrated his 5 year anniversary with Chief Carriers, although he didn’t always aspire to be a driver, for the last 16 years he has been driving trucks.  We sat down with Don to hear more about why he has dedicated the last 16 years to driving trucks and why loves driving flatbeds. 

The Beginning

Don’s early days in construction.

With a passion and love of music, Don started off his college career path studying music education and soon realized a career as a music teacher wasn’t going to pay well.   As a seeker of knowledge, this led Don to pursue a multitude of interests by completing many different certification programs in areas such as HVAC, Electrical, EMT, and Computer Science, just to name a few.  Don continued on his pursuit for knowledge and he decided to enroll at  Crown College in Saint Bonifacius, MN where he studied theology and communications. Prior to graduating, he was offered a job with Osmonics Inc. based out of Minnetonka, MN as a designer for their processes and packaging.  Osmonics manufactured robust reverse osmosis systems and was later sold off to GE.   Around 1998, Don was recruited by Parson’s Technologies to Cedar Rapids, Iowa as one of their programmers where they developed the Family Tree Maker software which was sold off to  From there he was recruited to MCI World Com which was sold off to Sprint.  After working with multiple companies where he stayed until they either closed and/or were bought out, he made the decision to be a freelance programmer and computer designer.  That new freedom and flexibility as a freelancer led him to residential and commercial construction to help supplement income between freelance gigs.  

Don’s Start in Trucking

In 2005, he was recruited by one of his previous colleagues from MCI with an opportunity to join CRST based out of Cedar Rapids, Iowa with the opportunity to become a Flatbed OTR Trainer.  Don spent over 10 years working for CRST and left the company to relocate back to northern Wisconsin which was too far off their travel lanes.   

After leaving CRST, he worked a few months at Gordon Transport and was offered to drive for Roehl Transport where he spent approximately a year when he was referred to Chief Carriers by another driver.   This driver referred Don to our recruiter because of his knowledge and sincere willingness to help a fellow driver that he did not even know.   Fast forward and Don is driving flatbeds. He has been one of Chief Carrier’s professional company drivers for the past 5 years.  That willingness to listen and help other drivers continues to this day.  

Proud To Be on Board

This past week, Don was presented with a certificate to celebrate his 5 year anniversary of driving flatbeds with Chief Carriers.   He was also recognized as one of the 2021 3rd Quarter High Milers.  Then add in that Don’s name has been mentioned often for his willingness to help, guide, and support fellow drivers in the fleet.   His past experience as a trainer shines through naturally.    

“All choices in my life – past & present – have been focused on optimization and efficiency for myself and those around me.  I believe in working smarter, not harder in all things.” ~ Don Wilkes III

Why Trucking?

A scenic view Don captured from the open road.

Don shared that one of the top reasons he decided to get into the industry was the overall income potential in being a driver versus the investment required to enter the industry.   For instance, It’s not like attending medical school yet offers the earning capacity of a general practitioner with very little required to enter the field.  Let’s not forget the freedom and flexibility to be on the road to be able to travel our country.  Driving a truck offers a great deal of variety.  That variety includes having an independent work environment, the mobility to go anywhere, being paid to spend time traveling, the constant change of scenery, change in climate, and that each load is different.  

My father always says: “Invest in memories.”  Having a long-term goal or a bucket list is all and good, but don’t miss out on the memories you could be making today. Take a hike, go camping, visit with friends & family. Don’t sacrifice today’s memories for a chance at tomorrow’s what-ifs.”

Why Flatbeds?

Don’s response was that it is pure math and physics.   Driving flatbeds isn’t the hard part, it is the loading, chaining, tarping, and being strategic to find the best possible way to safely secure the load.  The strategy is in planning the most efficient way to secure the load and each load is different.  Safety is a top priority whether on the road, at the terminal, loading, or unloading, it is always top of mind. 

When Not Driving a Truck

Now that technology allows us to be connected, entertained, and informed no matter where we are, there are endless possibilities of things to do for truck drivers when on the road.  Don shared the many gifts and talents that he enjoys doing while on and off the road. 

“I come from a family that values diversity…  Differing races, skills, beliefs, and goals make up the core of who we are.  Much like my family, I strive for diversity in my life.  While living over the road, I can be found creating art, writing, playing video games, or participating on various YouTube live stream panels. At home, I’m doing anything from crafting musical instruments, designing board games, DJing, sewing outfits, or even building a garage.  The possibilities are endless!  I love to create something that no one else does.  When asked why I pursue so many activities, I can only say:  Why not? Every person possesses limitless potential –  why not sample every opportunity?”


two make truck drivers standing with a woman

Don, his daughter, and his father.

Don has two grown children.   His oldest, Allie Wilkes is 22 years old and currently attending graduate school studying criminal psychology.  His son, Austin, is 19 years old and currently a combat engineer serving in the Marines

Don’s spoke often of his father and the stories of their upbringing and minimalist lifestyle growing up in northwestern Montana.   So it wouldn’t surprise you that his father, Don Wilkes Jr., is an outdoor enthusiast and hosts his own YouTube Channel called:  Sty North.   Don Jr’s channel hosts live streams where they discuss everything from hiking, camping, and his adventures in the Great Outdoors.  Don’s father has over 4,000 subscribers and has been hosting his YouTube Channel since 2015.  You will find an array of  “Sty Stories” and “Around the Campfire” talks while on Live Stream.  Don values his upbringing and the simple pleasures in life and that includes his family.   

male graduate and a female graduate standing next to each other

Don’s children Austin and Allie.

Don shared one of his father’s favorite sayings:   My father always says: “Invest in memories.”  Having a long-term goal or a bucket list is all and good, but don’t miss out on the memories you could be making today. Take a hike, go camping, visit with friends & family. Don’t sacrifice today’s memories for a chance at tomorrow’s what-ifs.”     

Bean On The Bay

a dog sitting in the cab of a flatbed truck

Bean on the outlook from the cab of a Chief Carriers truck.

This is Don’s travel companion, his sidekick and fur baby. Bean is a 6-year-old Boston Terrier that travels with his “Poppa Don”.  When not on the road they live on Lake Superior in Northern Wisconsin.   You can follow Bean’s Adventures on Facebook:

Drive For Chief Carriers

We’re incredibly proud of Don’s accomplishments personally and professionally. We’re grateful for his dedication to driving flatbeds for Chief Carriers and our clients.

If you are eager to find a career like Don’s that is both personally satisfying and financially rewarding, we encourage you to learn more about Chief Carriers. Chief is a family. We know each other here and every member of the office staff will stand behind you to make sure you’re successful. That includes providing you with outstanding equipment, maintenance and safety programs—because nothing is more important than getting you home to your family safe and sound. Click here to learn more bout driving a flatbed truck with Chief Carriers.