The Art Of The Sabbatical with Michael Remedios | Convos With Friends
In this conversation, I sit down with my friend and one of the best advisors I know, Michael Remedios, founder of Wonderland FP, to explore his journey through what he calls the "art of the sabbatical." Michael made the bold decision to leave a successful career as a lead advisor — at the height of his earning potential — to create space for reflection, experimentation, and eventually launching his own firm.
We start with the feeling that pulled Michael toward this decision — not a logical calculation, but an unsettled voice that grew louder over time. He shares how he spent a year quietly preparing for his sabbatical while still employed, traveling solo for the first time, picking up running, and experimenting with who he wanted to be, so that when day one arrived with nothing on his calendar, he wasn't starting from zero.
One of the things I love most about this conversation is how Michael reframes the sabbatical through a financial-planning lens. On a spreadsheet, it looked like a terrible decision — a 100% pay cut during peak earning years, less money invested, a longer path to financial independence. But he was tired of making every decision for a 65-year-old version of himself he doesn't even know yet. We dig into why financial planning needs to make room for this kind of mid-life optionality, and why saving for 40-year-old you might be just as important as saving for retirement.
We also explore the deeper personal layers of his journey — hitting every professional benchmark and still feeling lost, the "I'll be happy when" trap, working through it with a therapist, and what it really means to rewrite your definition of success from the inside out. Michael shares how the sabbatical wasn't about running away, but about learning what truly mattered to him, so he wasn't just replicating the same life with his own name on the door.
We close with a conversation about rock bottom, catching lessons early, embodying the future version of yourself now, and the belief that alignment in spirit, mind, and body is what allows everything else — including money — to follow.
Michael now does this work with clients at Wonderland FP, helping millennials navigate the big life moments — combining finances, starting families, buying homes — with intention and permission to live authentically. Check him out at wonderlandfp.com and find his Substack at The Art of Wandering.
Read the Art of the Sabattical on Substack
