6. Redefining Failure: How Bankruptcy, Burnout, and Big Risks Built a Life She Loves

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What if the things you fear most—failure, debt, burnout—aren’t the end of the story but the beginning of something better?

In this raw and honest episode, I sit down with digital marketer and multi-passionate entrepreneur Alyssa Tollefson to talk about the parts of the journey that don’t make it into most highlight reels. From bankruptcy to business pivots, motherhood to mindset shifts, this conversation goes beyond business to what it really takes to build a life on your own terms.

Alyssa shares how she went from taking over a restaurant at the start of 2020 (yes, right before the shutdown), to navigating six-figure debt, shifting into a boutique model, and eventually filing for bankruptcy—not as a failure, but as a strategic, life-affirming move that gave her family a clean slate.

If you’ve ever felt like quitting, questioning your decisions, or wondering if you’re “cut out” for this, this episode is proof that you’re not alone and you’re probably doing better than you think.

When Rock Bottom Becomes a Rebuild

When Alyssa took over a restaurant at the beginning of 2020, she couldn’t have predicted what would come next: a global pandemic, mounting business debt, and the crushing pressure of trying to hold it all together with a toddler at home.

What followed wasn’t a polished comeback—it was a gritty, imperfect pivot fueled by necessity, resilience, and resourcefulness. She turned the restaurant into a boutique, leaned on coaches and mentors, and ultimately made the hard (but wise) decision to file for bankruptcy.

This part of the conversation is about survival, yes—but also about how much strength it takes to ask for help, shift course, and rewrite what success looks like.

The Truth About Risk, Resilience, and “Starting Over”

We talk a lot in entrepreneurship circles about taking risks—but rarely about what happens when those risks don’t go the way we hoped.

Alyssa shares what she learned from running multiple businesses, including what it means to be scrappy, resourceful, and creative in the face of unexpected challenges. She also shares how filing for bankruptcy—something she once believed would be the worst thing that could happen—actually freed her up to move forward, protect her family, and rebuild with confidence.

More than anything, this part of the conversation is a reminder that real resilience isn’t about doing it all perfectly. It’s about making brave choices, even when they don’t make sense to anyone else.

Redefining Success (and Who Gets to Decide)

Alyssa’s definition of success used to look like a six-figure business, full creative control, and checking every box. Today? It looks like being present with her kids, feeling grounded in her work, and knowing she has the skills and confidence to pivot whenever she needs to.

We talk about how much noise there is around what success “should” look like—and how powerful it is to shut all of that out and ask yourself what you actually want.

If you’ve been stuck in comparison mode or feeling behind, this part of the episode will help you get honest about what success really means for you.

What You’ll Learn in This Episode:

What Alyssa learned from losing her business—and how she turned it into a new beginning
→ [01:00]

Why bankruptcy isn’t the end—and how it helped her protect what mattered most
→ [20:10]

How to stay resilient when nothing goes as planned (hello, COVID, layoffs, and kids!)
→ [12:30]

The importance of mindset, community, and asking for help—even when it’s uncomfortable
→ [05:15]

How Alyssa’s redefining success—and how you can too
→ [34:30]

Meet Alyssa Tollefson

Alyssa is a digital marketer, speaker, and creative entrepreneur based in Wisconsin. After navigating the highs and lows of entrepreneurship—including running a restaurant, launching a boutique, and filing for bankruptcy—she now helps boutique owners, salons, and small business owners build standout brands and online presence, with "unsolicited marketing advice" on her social media channels.

She’s a mom of three, a full-time marketing pro, and someone who isn’t afraid to talk about the messy middle.

Learn more at alyssatollefson.com
Follow her on LinkedIn and Instagram.

Final Thoughts: Failure Isn’t the End—It’s Part of the Process

If you’ve been holding back because you’re afraid of what might go wrong, let this episode be your reminder: You will figure it out.

It won’t always be easy. It probably won’t be pretty. But as long as you stay grounded in your values, stay open to change, and trust your capacity to rebuild—you’re never really starting over. You’re starting again, but with more wisdom this time.

🎧 Tune in now to hear Alyssa’s story and feel a little more seen, a little more steady—and a lot more capable of rewriting your own.