At some point in the entrepreneurial journey, a shift happens.

Maybe the business isn’t sustainable anymore.

Maybe the founder has outgrown it. Or it has outgrown them.

Or maybe, for the first time in a long while, stability feels more appealing than hustle.

Whatever the reason, more entrepreneurs are finding themselves on a new path. And that is looking for a job.

It’s a decision that can be full of mixed emotions. Relief. Uncertainty. And sometimes, even shame.

But here’s the truth: Seeking a job after running a business, or even while running it, isn’t a failure. It’s a transition. And like any transition, it comes with its own set of challenges and opportunities.

Why Would an Entrepreneur Want a Job?

Entrepreneurs don’t just wake up one day and abandon their dreams. The decision to pursue traditional employment is often deeply intentional.

For some, it’s about financial stability after a tough season. For others, it’s a chance to learn from the inside – to gain perspective, tools, or connections they couldn’t access on their own. Many are simply ready for a slower pace, a steadier rhythm, or a new kind of fulfillment.

There’s also the very human truth that people evolve. Just because someone was a founder doesn’t mean they’ll always be one.

The Challenges of Transitioning to Employment

Still, the job search process can be uniquely frustrating for former or current entrepreneurs.

That’s because résumés don’t tell the whole story. It’s hard to summarize the role of “founder,” especially when it spans marketing, operations, leadership, and growth strategy all at once.

Hiring managers may also be wary. Some assume that entrepreneurs can’t take direction or won’t stick around.

Imposter syndrome can also creep in. It’s easy to feel like your nontraditional path isn’t “enough,” especially when facing a wall of corporate job postings.

And then, there’s often emotional baggage. Burnout. Guilt. A sense of loss.

Perhaps most of all, there’s the question of how to explain it all. How can you write a résumé or cover letter that translates years of grit and vision into something employers will actually understand and value?

There’s Help. And You Don’t Have to Do It Alone.

That’s why Sacred Fire Creative’s Malee Ojua and Clearinity’s Conrad Rohleder are launching a new in-person event series called Job Searching for Entrepreneurs. This event is designed to help entrepreneurs on the hunt for jobs to be more successful in this endeavor. It’s for founders and freelancers who are wondering how to reshape their stories, rebuild their confidence, and take a meaningful next step toward traditional employment without compromising who they are.

The first session, happening on July 29, 2025, at Offbeat Coffee in Salem, OR, is all about building a résumé and cover letter that works.

Together, Conrad and Malee will walk you through:

• What to include in a resume when you’ve worn all the hats
• How to write a cover letter that feels honest and grounded
• Common mistakes entrepreneurs make in the job hunt
• How to own your story, even if it doesn’t follow a “standard” path
• Reframing the transition as growth

This session will be warm, practical, and real. It’s not a career coaching seminar. It’s a conversation among peers.

About Conrad Rohleder

Conrad Rohleder is a seasoned business strategist and entrepreneur who passionately builds people-first systems across diverse sectors – from tech startups and nonprofit leadership to local community initiatives.

As the founder and CEO of Clearinity, which he launched in early 2018, Conrad has helped hundreds of e-commerce companies scale sustainably by addressing operational pain points, especially in inventory and change management systems.

Conrad is deeply versed in systems thinking, organizational change, and emerging technologies like AI, and he’s gone through multiple career transitions himself. His unique blend of empathy and real-world insight helps professionals reframe their résumés, rethink their processes, and align their work with what truly fits their lives, not just their job titles.

A New Chapter Starts Here

If you’re a founder or self-employed professional thinking about the next step, or already deep in the job search, Job Searching for Entrepreneurs is for you.

You’re not starting over. You’re starting with experience.

And with the right tools and support, this next chapter can be just as meaningful as the last.

Reserve your free spot today.