Charlie Wilshire has spent more than three decades strengthening his community through creativity, education, and service. From transforming homes across Oregon to mentoring students, Charlie Wilshire’s career has been defined by learning, leadership, and craftsmanship.
He is the owner of The Merry Craftsmen, a business that has specialized in home remodeling projects for over 32 years. Before and alongside his work in construction, Charlie Wilshire built a career in education, teaching language arts and social studies at both traditional and alternative schools. His teaching journey included positions at Kennedy High School, Northwest Youth Corps Outdoor High School, and Agnes Stewart Middle School, where he designed curriculum, led literacy programs, and mentored future educators and AmeriCorps volunteers.
Beyond his work in construction and education, Mr. Wilshire has always sought ways to invest in his community. He volunteered with SMART Reading to support early literacy and served as a regional director for the Oregon Middle Level Association, advocating for middle-grade educators and students.
What is your typical day, and how do you make it productive?
My typical day involves reviewing the myriad projects I am involved in, contemplating how I am going to prioritize them and strategizing how I may find success with several of the goals for the day. I then set reasonable goals to accomplish the construction tasks I set out to do and, with fortune, get them done.
How do you bring ideas to life?
I bring ideas to life by first dreaming about them and working through the many angles involved in their manifestation. I talk about them with those who I trust will not immediately cut me down and then attempt to create an action plan that has a series of subgoals that are manageable so that I may eventually reach higher plateaus that get me closer to the overarching goal.
What’s one trend that excites you?
A trend that excites me is seeing how people are willing to exercise their democratic rights to peacefully voice their opinions and try to take charge of their communities’ futures.
What is one habit that helps you be productive?
The best habit to help me be more productive is regular physical exercise.
What advice would you give your younger self?
I would tell my younger self to stay motivated, dream big, and seek help from those who can help you reach your potential.
Tell us something you believe that almost nobody agrees with you on.
I believe in the power of humor to help make the world a better place.
What is the one thing you repeatedly do and recommend everyone else do?
I often make my way into the wilderness to connect with myself and the sublime, life-effulgent setting of our natural world.
When you feel overwhelmed or unfocused, what do you do?
I often find that I take deep breaths and repeat to myself that “and too this shall pass.”
What is one strategy that has helped you grow your business or advance in your career?
Talking straight with clients who seek to utilize my talents.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
I usually fail once a day at something yet attempt to see it as a blessing that in failing, one learns how not to do something while also learning humility. A big failure in my life is selecting a profession that others thought I should do, though I really did not want to do it despite the fact I would be good at it.
What is the best $100 you recently spent? What and why?
The best $100 I spent recently was on a steak dinner I prepared in the wilderness for my two friends while we explored a 40-mile section of an abandoned railroad winding its way through the coastal mountains of Northern Oregon.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
A favorite book is “Grapes of Wrath” by John Steinbeck, as it details the pain, endurance, perseverance, and grit of a family who show the reader where toughness begins and weakness ends. A favorite Podcast is “Radiolab’s” story about the recent scientific discoveries about the synergistic qualities of trees.
What’s a movie or series you recently enjoyed and why?
I just watched “Roofman” and loved it because it told my story in a revisionist way, where a person makes less-than-ideal choices yet always means well and seeks to make others’ lives better at the cost of his own.
Key learnings
- Be strong through trying to understand what it is like being in the shoes of those who you spend time with.
- Seek adventure to push your limits, as those limits are only new horizons from whence fresh perspectives are born.
- Listen to yourself with intent so you can respect the inner voice, which means respecting yourself—which means connecting one’s heart with one’s passions and talents.