Episode Title

From “I Bet I Could Make That” to Workboots & Glasses: D’ondra Howard on Courage, Creativity, and Starting Before You Feel Ready

Episode Description

Long before D’ondra Howard ever called herself a woodworker, she had a habit.

She would walk through furniture stores, study the pieces, look at the price, shake them, pick them up—and think, “I bet I could make that.”

At the time, she did not realize she was planting the seed for a completely different future.

D’ondra never set out to build a woodworking business. She had imagined a career in the medical field. But after buying a home, she began tackling projects herself—painting cabinets, pulling up carpet, laying floors, learning to use tools, and slowly proving to herself that the things she feared were often far more manageable once she actually began.

Small projects became small wins. Small wins became confidence.

Eventually, D’ondra moved beyond replacing furniture in her own home and started building for others. Her garage filled with orders until she could barely move through it. That led to another leap: renting a dedicated shop, taking on overhead, and trusting that the business could grow into the space she was creating for it.

Then came another evolution.

What D’ondra initially imagined as a furniture business expanded into Workboots & Glasses, where she now builds custom furniture, creates handmade gifts, and teaches woodworking workshops that help other people—many of whom have never touched a tool—discover that they can do hard things too.

Her journey is about more than wood. It is about fear, self-talk, learning by doing, surviving slow seasons, trusting the signs to keep going, and understanding that a dream can change shape as you grow into it.

For any woman standing in front of something unfamiliar and thinking, “I don’t know if I can do that,” D’ondra’s story offers a wonderfully practical answer:

Start.

Key Discussion Points

• 01:53 — D’ondra talks about the response to her woodworking classes and how one viral TikTok dramatically increased interest in learning from her.

• 03:09 — She shares how buying her home pushed her to confront her fear of tools and begin learning how to use them.

• 04:37 — D’ondra reflects on repeatedly looking at furniture and telling herself, “I bet I could make that,” long before she actually began building.

• 06:55 — She explains how entrepreneurship challenged the way she thinks about pricing, value, and separating her own buying habits from those of her customers.

• 08:44 — D’ondra describes outgrowing her garage and facing the fear of moving into a dedicated shop with rent, utilities, supplies, and new overhead.

• 10:01 — She looks back on the spaces that did not work out and realizes those “no’s” may have kept her from choosing a space that was already too small.

• 10:48 — D’ondra shares one of the lessons she learned from expanding: “You need to plan for the future, not where you are right now.”

• 12:13 — She explains that woodworking was never originally part of her career plan and that she first just wanted to replace IKEA pieces in her own home.

• 13:34 — D’ondra talks about redesigning her house while her husband was deployed, including painting cabinets, removing carpet, and laying floors herself.

• 16:26 — She recalls finding a step-by-step cabinet-painting guide and realizing the project was not as difficult as she had made it in her head.

• 17:38 — D’ondra explains how small projects and small wins gradually built her confidence to tackle larger challenges.

• 19:20 — She describes a difficult period after moving into her shop when one slow month became several and she began questioning whether she should continue.

• 20:03 — D’ondra shares how new orders repeatedly appeared just as she was considering quitting, giving her a reason to keep moving forward.

• 22:02 — She explains why helping nervous workshop participants discover what they are capable of is one of the most rewarding parts of teaching.

• 25:12 — D’ondra outlines the woodworking classes she offers, including cutting boards, epoxy projects, multiweek builds, one-on-one instruction, and private groups.

Notable Quotes

“I bet I could make that.”

“You need to plan for the future, not where you are right now.”

“It started with small projects, small wins that I was like, ‘Okay, cool, I can do that.’”

“But you won't, you won't know that unless you do it.”

“You just have to have somebody who has trust in you to say, ‘You got this.’”

“Start. Whatever you think you want to do, try it out.”

Takeaways

• Confidence can begin before skill. D’ondra spent years telling herself she could make things before she actually knew how.

• Small wins create momentum. Each project she completed made the next unfamiliar challenge feel more possible.

• Fear often gets smaller once you start doing the thing you were afraid of. D’ondra repeatedly discovered that projects became easier as she worked through them.

• Growth may require planning beyond your current circumstances. Moving from a garage into a larger shop taught D’ondra to think about where the business was going, not only where it was.

• Difficult seasons do not automatically mean the dream is over. During slow months, D’ondra questioned whether to continue, but new opportunities kept reminding her why she started.

• A dream can evolve. What began as a desire to build furniture eventually expanded into teaching other people how to build for themselves.

• Encouragement matters. D’ondra sees firsthand how hearing “You got this” can help someone move through fear and accomplish something they did not believe they could do.

Connect with Guest

Website: https://www.workbootsandglasses.com/

Instagram: https://www.instagram.com/workbootsandglasses
@workbootsandglasses

Email: hello@workbootsandglasses.com

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