OE Spotlight: Michael Bailey, The Man with the Magical Ties

Meet Michael Bailey, a dedicated estate planning attorney who brings the office to you… literally. As a mobile estate planning attorney, Michael travels to clients across the Denver area, helping them prepare for the future with personalized care and convenience. From wills and trusts to financial and medical powers of attorney, his goal is to ensure every client feels confident and secure in their plans for the years ahead.

And while his work revolves around life’s biggest responsibilities, Michael brings a touch of charm to every meeting, often in the form of one of his magical ties.

Finding Purpose Through Helping Others

For Michael, estate planning isn’t just a legal service—it’s an opportunity to make a meaningful difference.

“This area of law really allows me to help people and work collaboratively with them,” he explains. “Many areas of law involve conflict or adversarial relationships, whereas estate planning allows me to work side-by-side with clients to accomplish their goals.”

That collaborative spirit has paid off. Over the past year and a half, Michael has tripled his business volume and revenue, published a book on estate planning (available on Amazon), and received countless handwritten thank-you notes from appreciative clients—a true testament to the care and trust he builds with every interaction.

Words of Wisdom for New Attorneys

His advice to others entering the field reflects the same steady patience found in his work, and perhaps in the way he curates his growing tie collection.

“It will take time to grow your business. Find good, solid referral partners and be patient. Growth won’t happen overnight, but if you stay steady, it will come.”

How Office Evolution Helps Him Thrive

One of the biggest advantages of being part of the Office Evolution Greenwood Village community is flexibility.

“I can meet clients at offices all across the Denver area, so I can travel to locations closer to where they are,” he says. “It makes the process much more convenient and comfortable for them.”

That convenience, paired with a friendly smile and one of his signature ties, helps set Michael apart. Whether he’s meeting clients in Greenwood Village, Cherry Creek, or Boulder, he brings professionalism, empathy, and a bit of personality to every visit.

A Day in the Life

A typical day includes four to five client meetings, either consultations or document signings, plus time spent reviewing drafts, returning calls, and handling emails between appointments. Because not all meetings happen in the same place, Michael spends plenty of time on the road, taking his “mobile office” wherever it’s needed most.

Beyond the Office

When he’s not helping clients, Michael keeps just as busy supporting his kids’ activities. His middle daughter plays competitive volleyball and performs in marching band, while his youngest son plays competitive basketball.

Michael also referees high school basketball games, enjoys reading and hiking, and every holiday season transforms his home into a glowing wonderland with over 25,000 Christmas lights—plus a few Halloween surprises, of course.

A Tie for Every Occasion

If you’ve seen Michael around Office Evolution, you’ve probably noticed his impressive, ever-changing tie collection. It all began years ago at a garage sale, where a retired banker was selling ties for $2 each.

“I found quite a few I liked, and the collection just grew from there […] I wear ties that match the season or holiday—Christmas, Thanksgiving, Halloween, Easter, you name it.”

From festive snowmen to patriotic stripes, Michael’s ties have become a signature part of his professional identity. His favorite? A snowman tie he shares with his son:

“We wear matching ones in December, it makes me happy every time.”

And maybe that’s the real magic behind Michael’s ties: they aren’t just accessories—they’re little reminders of joy, connection, and the importance of bringing your full, authentic self to your work.

Inspiration and Gratitude

Michael credits his father and mentor, Wayne Stewart, as two of his biggest influences.

“My father always worked hard and put his children first, he taught me what it means to care for your family. Wayne helped me as a young attorney, just because it was the right thing to do. That kind of generosity still inspires me.”

Part of a Supportive Community

When asked what he values most about Office Evolution, Michael doesn’t hesitate:

“I always enjoy having people around who are willing to support me and my business. Whether it’s the staff or other members, I feel like I have friends here, and I’m never alone.”

Just like his ties, Michael’s presence adds a little extra color and warmth to the Office Evolution Greenwood Village community—proof that a professional touch, paired with a bit of personality, can truly go a long way.

Get in Touch with Michael Bailey

Put your best tie on and get in touch with Michael Bailey today!

And don’t forget to purchase The Mobile Estate Planner: Michael’s Practical Guide to Estate Planning in Colorado on Amazon!

Buy the book on Amazon