top of page

LOOPED

A Quest

From the Straits of Macinac to the Bitter End

An upcoming memoir of adventure, reinvention, and a journey beyond the horizon.

Discover the StoryContact the Author

8,000

MILES TRAVELED

53ft

SAILBOAT

43

CHAPTERS

1784044664.png

A midlife crisis, a 53-foot sailboat, and eight thousand miles of open water

Looped is Timothy Skillman's memoir. It follows a father, husband, and successful business consultant as he stumbles, then falls, into a midlife crisis. In search of what we all crave, answers, purpose, adventure, or a memorable death, Tim walked away from an idyllic life. He quit his high-powered crisis-management partnership and left his home with no plans to return, ever.

Moving aboard his 53-foot sailboat, he set out with no clear plan to return. What followed was a year-long loop from the Great Lakes to the Eastern Caribbean and home through New York and the Erie Canal — a journey shaped by storms, river locks, strangers, risk, humor, and a relentless need for peace.

DISCOVER THE BOOK

THE JOURNEY

One boat, roughly eight thousand miles, and a year on the water. Down through the heart of the continent, out to the islands, and home again by a different road, closing the loop.

THE ROUTE

ChatGPT Image Aug 12, 2026, 12_52_28 PM.png

This is a stylized chart, not a navigational map. Distances and coastlines are illustrative.

Out one way and back another, until the wake finally met itself and the loop was complete.

THE JOURNEY

One boat, roughly eight thousand miles, and a year on the water. Down through the heart of the continent, out to the islands, and home again by a different road, closing the loop.

THE ROUTE

ChatGPT Image Aug 12, 2026, 12_52_28 PM.png

This is a stylized chart, not a navigational map. Distances and coastlines are illustrative.

Out one way and back another, until the wake finally met itself and the loop was complete.

Lawrence ADS (15).png

A Life Drawn to the Water

Raised on Lake Angeles north of Detroit, Timothy Skillman developed an early passion for sailing, independence, and risk.

After earning two degrees from the University of Michigan and spending twenty years building a successful career, he left conventional life behind and moved aboard his boat. Moving through time and space in new and unusual ways remains his passion. Life on the edge is his preferred location.

MEET TIMOTHY

ABOUT TIMOTHY

Social & Video

Follow the Journey

INSTAGRAM

Images from the journey

LINKEDIN

Author & Professional updates

full cover 5 (2).png

YOUTUBE

Stories from a life on the water

Open Timothy's video channel.

FOLLOW ALONG

Media & Social

Follow Timothy across his existing platforms. Interviews, videos, reviews, podcasts, and speaking appearances will be gathered here as they happen.

Timothy Skillman

Author of Looped, a memoir of an 8,000-mile voyage, a midlife course correction, and the search for a life beyond the horizon.

Explore

Follow

LinkedIn

YouTube

Facebook

Instagram

bottom of page