Michael Bosstick’s Picks: 3 Books for When You Don’t Know What You’re Doing With Your Life

“Many people are wandering through life, pretending like they have it all figured out,” Michael Bosstick says on a recent episode of The Skinny Confidential Him & Her Show. As his wife and cohost Lauren prepares to return from maternity leave, Bosstick dedicates his closing solo episode to addressing what many listeners quietly wrestle with—what to do when life feels overwhelming or directionless: “There are many people struggling just as much as you.”

From career burnout to dating frustrations, relationship ruts, health setbacks, and parenting chaos, he offers practical strategies mixed with stories from his own path. “If you’re somebody who’s feeling a little bit lost in life, maybe in every area, maybe just in one or two areas, this episode’s for you,” he tells listeners.

Stop waiting for passion to strike

For many young adults, the constant advice to “follow your passion” can feel more like a burden than inspiration. Bosstick recalls how frustrating it was in his 20s and early 30s to hear mentors insist that passion would make work effortless. “That’s great advice for people that have already found their passion,” he admits. “For me it was much harder. I had so many different interests. I was scattered all the time. I couldn’t focus on one thing or the other.”

Instead of waiting for one lightning-bolt answer, he experimented. Bosstick dabbled in real estate, aviation, client services, and eventually podcasting and media, each step teaching him what he didn’t want and slowly pointing him toward what truly energized him. “The way that I figured out what the thing was, was I started tasting and trying and doing a lot of different things,” he explains.

He reassures listeners still feeling aimless: Lacking one clear passion doesn’t mean you’re behind. Each attempt—even jobs that didn’t feel like the right fit—can create breadcrumbs that lead you closer to meaningful work. “Don’t feel discouraged,” he says.

Comfort doesn’t protect you from burnout

Bosstick knows firsthand how tempting it is to stay in a high-paying role that makes you miserable. He warns that financial comfort alone doesn’t shield you from burnout. “Maybe you’re doing really well financially, but you hate your career and you hate your job and you don’t like your boss and you’re burned out,” he says. “If it were me…I would say take less money for something you’d be happier doing.”

His advice is direct: Map out what energizes you versus what drains you. If the scales tip heavily toward draining tasks, that’s a sign change is needed—whether through a new opportunity or a conversation with leadership about shifting responsibilities. “If you don’t raise your hand and you don’t speak up for yourself, nobody else will,” he adds. “If you can be comfortable making 60K doing what you love versus 80K doing what you hate, I would definitely take the 60,” he explains. That trade-off, he argues, pays dividends in mental health, energy, and long-term sustainability.

“It can’t always be the dating apps”

Turning to dating, Bosstick acknowledges it’s been years since he was single, but he’s seen enough patterns among friends and siblings to know the challenges are real. Still, he insists that external factors can’t be the only explanation for dating struggles. “It can’t always be the other people. It can’t always be the dating apps. It can’t always be the environment,” he says. “The reason I say that confidently is because many people are getting into relationships and many people have found love.”

His advice starts with an honest audit. He suggests journaling why past relationships ended, looking for repeated patterns, and questioning whether personal “must-haves” are actually narrowing the dating pool unnecessarily. “Sometimes people create these scenarios where instead of going after a hundred percent of what’s available to them, they’ve created this kind of narrow framework where like, now there’s only two percent of the people that could fit that box,” he explains.

Don’t lose yourself in the parenting process

As a father of three, Bosstick doesn’t sugarcoat the strain parenting brings. But his perspective is clear: Parents shouldn’t lose themselves entirely in the process. “We all want to take care of our kids…but they need to integrate into our lives, not the other way around,” he stresses.

That mindset, he says, prevents burnout and resentment. While prioritizing children is natural, overextending can erode both personal well-being and relationships. He emphasizes that maintaining a strong partnership sets the best example for kids. “Children thrive in a loving environment where they see their parents connected and intimate,” he notes.

Building your support system

Bosstick closes the episode by reassuring listeners that uncertainty is universal, then offers concrete resources. His solution is to immerse yourself in stories and examples that inspire. He recommends Viktor Frankl’s Man’s Search for Meaning, James Clear’s Atomic Habits, and Michael Singer’s The Untethered Soul as books that can help reframe directionlessness into possibility. Consuming uplifting, practical content, he explains, helps “strip out the traits, the habits, the patterns” that others have used to overcome similar struggles.

Above all, Bosstick stresses the importance of community—whether through mentors, friends, or support groups. Join Bossticks community by listening to the rest of The Skinny Confidential Him & Her Show, out now wherever you listen to your podcasts.

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