Episode 204: The Moment I Knew: Joss Richard (author)

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Find our guest, Joss Richard here.

Career paths are rarely as straight as we think they’re supposed to be.

Sometimes the job that once felt exciting starts to feel too small.

Sometimes the career that looks impressive from the outside no longer feels fulfilling on the inside.

Sometimes the thing you worked so hard to build is not the thing you’re meant to keep building forever.

In this episode of The Business Reboot Podcast, we sit down with bestselling contemporary romance author Joss Richard for a candid conversation about career pivots, personal fulfillment, entrepreneurship, risk, and what it really means to bet on yourself.

Before becoming a bestselling author, Joss spent years behind the scenes in television, producing for shows like The Ellen DeGeneres Show, Red Table Talk, and Reese’s Book Club. It was a career many people would consider a dream.

But in 2024, Joss made a major career pivot. She left television to write full-time.

That decision came with real questions, real financial risk, self-doubt, hard conversations, and the kind of courage required when you know the safe thing is no longer the most aligned thing.

Her story is a powerful reminder for entrepreneurs, creatives, and business owners: reinvention is not failure. Sometimes it is the most honest next step.

When a Dream Career No Longer Feels Like the Dream

One of the most relatable parts of Joss’s story is that she was not leaving something that looked broken.

She had experience.

She had an impressive resume.

She had worked in spaces many people would love to be in.

But external success and internal fulfillment are not always the same thing.

That tension is something so many entrepreneurs understand.

You can have the clients, the title, the revenue, the reputation, the opportunity, or the career path that makes sense on paper — and still feel a quiet tug that something needs to change.

That does not mean you are ungrateful.

It does not mean you failed.

It may simply mean you are paying attention.

Career pivots often begin in that uncomfortable middle place where things are technically working, but no longer feel fully aligned.

For Joss, writing had become the thing that felt most alive. And eventually, she had to decide whether she would keep building the life she had known or take the risk of stepping into the life she wanted to pursue next.

The Courage to Bet on Yourself

Betting on yourself sounds inspiring when people say it after the risk has already worked.

It is much harder when you are standing in the middle of the decision.

For Joss, leaving a stable full-time job to write was not a casual choice. It involved financial risk, timing, uncertainty, and honest conversations about what was possible.

One of the most powerful pieces of the episode centers around the encouragement she received from her husband, who reminded her that she could find another job at any point in her life — but the opportunity in front of her might not come the same way again.

That question helped her see the moment differently.

Not as reckless.

Not as irresponsible.

But as an opportunity to take herself, her work, and her writing seriously.

For business owners, that part of the conversation is especially important.

There are moments when you do not need more proof that the pivot is safe.

You need to decide whether the cost of staying the same is becoming too high.

Career Pivots Are Not Proof of Failure

One of the themes throughout this episode is that a pivot is not always a breakdown.

Sometimes it is discernment.

Sometimes it is maturity.

Sometimes it is the natural result of growth.

That is a common pattern for entrepreneurs.

The business or career you build in one season may not be the one you are meant to carry forever.

An offer can still sell and no longer fit.

A career can look impressive and no longer feel fulfilling.

A business model can be profitable and still feel too heavy.

A pivot does not erase what came before it. It builds on it.

The experience, relationships, skills, confidence, and perspective you gained in one season often become the foundation for the next.

Redefining Success on Your Own Terms

In this episode, Joss also talks about the moment she knew she had “made it.”

For her, there were meaningful milestones: writing full-time and hitting a bestseller list. But like many entrepreneurs and creatives, she also acknowledged that the goalpost can keep moving.

That is one of the complicated parts of success.

You reach the thing you once dreamed about, and then almost immediately, a new marker appears.

More sales.

A bigger audience.

A better launch.

A stronger year.

A more impressive title.

A higher level of visibility.

We talk often about the importance of defining success before the internet defines it for you.

Because if you are not careful, you can build an entire business or career around someone else’s version of “making it” and still feel disconnected from the life you actually wanted.

Success might include revenue.

It might include recognition.

It might include creative freedom.

It might include time with your family.

It might include work that gives you energy instead of constantly draining it.

It might include relationships, flexibility, faith, rest, and the ability to wake up excited about what you are building.

The point is not that there is one right definition.

The point is that you are allowed to define it for yourself.

The Role of Support During a Pivot

Another important part of Joss’s story is the role support played in her decision.

Entrepreneurship and career reinvention can feel deeply personal, but they rarely happen in isolation.

The people around you matter.

Supportive spouses, trusted friends, business partners, mentors, clients, and communities can help you hold courage when your own confidence feels shaky.

That does not mean the risk disappears.

It means you are not carrying it alone.

For Joss, her husband’s belief helped her take the next step.

For us, relationships have been central to the way they built The Business Reboot. In the episode, we reflect on our own desire to build a business rooted in real relationships, not a model where people are forgotten once they stop paying.

That kind of values-driven business model matters.

Especially in a world where so much business advice can feel transactional, automated, and overly focused on scale at the expense of care.

Trust is still a differentiator.

Relationships still matter.

And the way you choose to build your business should reflect what you actually value.

What Entrepreneurs Can Learn from Joss Richard’s Story

Joss’s journey from television producer to bestselling romance author is specific to her, but the lessons apply far beyond publishing.

For entrepreneurs and business owners, this conversation is a reminder that you are allowed to ask better questions about your work.

Not just:

Can I keep doing this?

But:

Do I want to keep doing this this way?

Is this still aligned?

What feels heavy that used to feel exciting?

What version of success am I chasing?

What would it look like to bet on myself in this season?

What would I build if I stopped assuming I had to do it the way I always have?

Those are the kinds of questions that lead to meaningful business growth.

Not just bigger growth.

Better growth.

More aligned growth.

Growth that supports the life you actually want.

If You’re Feeling Stuck, Pay Attention

If you are an entrepreneur feeling stuck inside a business that technically works, this episode is worth listening to.

You may not need to burn everything down.

You may not need to make one dramatic, overnight decision.

But you may need to pay attention to the places where your business, career, or definition of success no longer fits.

Sometimes being stuck is not a sign that you are failing.

Sometimes it is a sign that you are ready for the next honest move.

That might mean changing your offers.

Simplifying your business model.

Building more sustainable systems.

Reworking your messaging.

Creating more space for creative work.

Letting go of something that no longer fits.

Or finally admitting that the path you are on is not the only path available to you.

Career pivots are not always easy.

But sometimes they are necessary.

And sometimes, the next version of your work begins when you decide to bet on yourself.

Listen to Episode 204 with Joss Richard

In this episode of The Business Reboot Podcast, we talk with bestselling contemporary romance author Joss Richard about career reinvention, leaving a dream job, writing full-time, redefining success, building a values-driven path, and having the courage to pursue work that feels more aligned.

Whether you are considering a career pivot, navigating a business shift, or simply wondering whether the thing you built still fits the life you want, this conversation is a reminder that it is never too late to choose a more honest version of success.

Listen to Episode 204 of The Business Reboot Podcast wherever you get your podcasts.