An Inside Look at the Exhilaration and Terror of Life Outside the Box

The joys and challenges of a life that doesn't conform to society's expectations

Photo by Random Thinking on Unsplash

Sometimes a new life is a choice, sometimes it's a necessity, but it's always an adventure. - Allegra Chapman

Truer words were never spoken. My first new life was a choice; my husband and I vacationed on Maui and loved it so much we moved there. The second was a necessity; we lost our jobs and had to find new ones.

Allegra Chapman

invited me to reflect on both experiences as part of her “living outside the box” interview series.

I’m sharing excerpts from that interview here; to get the rest of the story (and info about her free creative wellbeing workshop on August 29), read her post:

Living Outside the Box with Wendi Gordon

If you’d like to share your experience in a “Living Outside the Box” interview with

Allegra Chapman

, use this form to submit your information to her. To read more interviews and other great content, subscribe to her newsletter.

Tell us about your “outside the box” life.

I have had two different "outside the box" lives. The first one started in 2001 when my husband, Steve, and I vacationed on Maui. We loved it so much we … moved to Maui in 2002. We did not have jobs or a place to live lined up in advance (and knew our former careers … were not possible on Maui). We signed a one-year lease within a week of our arrival and both found work within a month.

We lived on Maui for ten years … [and] our jobs involved booking activities for tourists. That meant we got to go to every luau, on every boat trip, zipline, etc. for free so we could … help tourists choose the best ones for their interests and budgets. It was wonderful, but there were no viable options for career advancement. …

We moved … to Texas, to serve as co-pastors of a church … and expected to stay there until we retired. But, in 2020, our second "outside the box" life began. …

[O]ur church council "asked" us to resign unexpectedly. We were both in our mid-50s ... At first, we planned to continue our careers as pastors [but that didn’t work out].

… It was very difficult for either of us to find other traditional full-time employment. …I became a freelance writer. I also have several very part-time remote jobs: peer listener, SAT/ACT exam prep tutor, and church office administrator. …

Those were two very different experiences - how did your feelings, and those of your families, differ about each one?

The first decision … was made because we fell in love with Maui, its people, and the marine animals. … We wanted less stressful jobs and more time for fun activities. It felt exciting, liberating, and we were impatient … [to] make that move to Maui.

The second was … brutal both financially and emotionally. It still is, but it's also liberating. We are … able to set our own schedules … and we don't have to do things we consider unethical or stay silent when others do them.

In both cases, our families of origin did not understand. … It's been much harder this [second] time. … We saw ourselves as failures… [and] had internalized our families' and culture's beliefs about what adults must do to be responsible and successful. …

What lessons have you learned from taking an “unconventional” path?

I've learned that I'd rather live with financial challenges than sell my soul and sacrifice my happiness to have a higher or more consistent income. I'd rather disappoint other people than ignore my own wisdom about what's best for me. I've learned that there are plenty of other people who agree and have found ways to create lives they love. I've learned that it takes courage, determination, and patience to forge a new path but it is possible and worth the time and effort.

What advice would you give to anyone considering an “outside the box” life?

… Don't fall for the "get rich quick" lies from people who promise to show you exactly how to earn as much as they do if you buy their courses or coaching services. No two people are identical, technology changes rapidly, and what worked for them is unlikely to work for you, for multiple reasons. … Start small, learn and grow and experiment while you still have enough income (or savings) to support you …

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Is your life “outside the box” in some way? If so, what lessons have you learned and what advice would you give? Normally only paid subscribers can comment (to keep this space as safe and supportive as possible), but anyone can on this post.

P.S. If you need encouragement to get out of a box you’re stuck in and move in a new direction, check out my “Nature + Nurture” ebook. A few sample pages:

Image credit: Wendi Gordon