Articles Tagged with: job searching

Job Searching as an Entrepreneur: Why You Don't Need to Go It Alone

Job Searching as an Entrepreneur: Why You Don’t Need Go It Alone

You were prepared for change.

You knew this next chapter wouldn’t be easy.

But nothing quite prepares you for job searching when you’re an entrepreneur.

You thought your biggest challenge would be updating your résumé.

Instead, it’s the quiet, grinding uncertainty that no one warned you about.

The job search isn’t just a search. It’s a test of resilience.

You apply for roles that sound like a fit. You try to explain what you did as a founder without sounding like you’re overqualified – or worse, like you’re starting over after what the interviewer may assume as a failure.

You wonder if the recruiter on the other side understands what it meant to build a brand from nothing, lead a team, manage budgets, grow revenue, solve crises.

You wonder if they can see the value behind the title of “Founder.”

You hit submit and wait. And wait. And wait.

Sometimes there’s a rejection. More often, just silence.

You start to question your instincts.

You rewrite your story. Again.

You try to stay upbeat for the next interview, even as your confidence thins.

And you begin to ask: Is it just me? Am I doing this wrong?

It’s not just you. And you’re not doing it wrong.

Job searching as an entrepreneur is uniquely challenging.

Not because you lack skills, but because traditional hiring systems aren’t built to understand non-traditional paths.

But here’s what no one tells you: You don’t need to muscle through this alone.

You don’t have to.

The missing piece in your job search might not be a better resume or a new strategy.

It might be a support circle, a space where you’re reminded of what you bring to the table, even when the world feels unsure of where to seat you.

What can support circles do for you?

A strong circle doesn’t just offer encouragement. It changes the experience of job searching as an entrepreneur in real, tangible ways.

First, you gain clarity. Talking with others helps you see yourself and your transferable skills more clearly.

You also learn how to tell your story. A support group helps you shape your founder journey into a compelling narrative that hiring managers can understand.

You get unstuck. Whether it’s a new connection, a practical tip, or just someone who’s been there, the right support gives you momentum.

Lastly, you feel human again. Being around others who get it helps you shake off the isolation, the imposter syndrome, and maybe even the shame that job searching can trigger.

You’ve carried enough alone. It’s time to let someone help you.

Finding the right support is what Job Searching for Entrepreneurs is all about. It’s not another job-searching, resume-writing workshop.

It’s a gathering place for people who are in the thick of the search, who’ve been refreshing job boards, second-guessing themselves, and wondering what’s next.

It’s a chance to talk about what really makes a difference: connection, community, and support that actually understands where you’re coming from.

In the upcoming session of this conversation, titled “Finding Support as a Job-Searching Entrepreneur,” we’ll explore:

What makes the job search uniquely hard for founders
How to find the right people to walk this path with you
Where to look for mentorship, guidance, and belonging
How to ask for help in a way that feels empowering

This session is on August 19, 2025, at Offbeat Coffee in Salem, OR, co-facilitated by Conrad Rohleder of Clearinity and Malee Ojua of Sacred Fire Creative.

The job search is hard.

But you don’t have to do it alone.

And you were never meant to.

Join us for this part of Job Searching for Entrepreneurs.

Let this be the session that reminds you that you’re not stuck.

You’re evolving. And there are people who see what you bring, even when the hiring algorithm doesn’t.

Joining is free. RSVP today.

How to Ace the Job Interview as an Entrepreneur

For years, your job interview was a client pitch.

You didn’t talk about your job qualifications. Instead, you showed them.

You didn’t wait to be hired to show what you can do. Instead, you built a business around what you can do.

You wore every hat, made every decision, and held the full weight of success (and failure) on your shoulders.

But now, something has shifted.

Maybe you’re craving stability. Maybe you’re burned out. Or maybe, for the first time in a long time, you’re curious about what it might feel like to be part of a team again – this time, not as the leader, but as a contributor with clear boundaries, shared goals, and room to breathe.

And that’s brought you here: preparing to reenter the world of traditional employment.

But let’s be honest. Job interviews hit differently when you’ve been the boss.

In the first part of this blog series, we talked about the resume and the cover letter. Here, we’re going to tackle the job interview.

Why Interviews Are Uniquely Challenging for Entrepreneurs

When you’re used to creating your own opportunities, sitting across from someone evaluating your qualifications can make you feel vulnerable, even strange.

There’s a quiet fear underneath.

Will they understand my story? Will they think I failed?

Am I too much? Or not enough?

These are common and completely normal questions for entrepreneurs making this leap.

Here’s why the interview stage can feel especially hard:

Your career path is nonlinear. Traditional roles follow a ladder. Yours was more like a jungle gym.
You’re afraid they’ll think you can’t follow. You’re no longer the CEO, but that doesn’t mean you can’t thrive in a supportive role. Still, that transition can be hard to communicate.

What Hiring Managers Need to Hear

You bring incredible value to the table. But it’s up to you to make that visible.

Here’s how to make your experience resonate in the interview:

Reframe your story.

Don’t just say, “I ran a business.” Translate it.

I launched and scaled a client-focused brand, led a team of five, managed a $100K budget, and built a marketing system that generated consistent leads through organic social media.

Be specific with your story and focus on outcomes. Connect your experience to the job you’re applying for.

Address the elephant in the room.

If your business closed or paused, acknowledge it confidently.

After several meaningful years in entrepreneurship, I’m choosing this next chapter intentionally. I’m excited to contribute in a focused role where I can apply my experience and collaborate with a team.

Most employers aren’t put off by your business pausing, closing, or being set aside. They just want to understand your “why” and know you’re ready to show up fully.

Shift the narrative from “boss” to “team player.”

One of the biggest assumptions you may face is that you won’t take direction or adapt well to the hierarchy.

Prove them wrong by sharing examples of collaborative partnerships, taking client feedback, and learning from mentors or peer networks.

Let them see your willingness to grow within a team, without needing to lead everything.

Use the STAR Method to Tell Compelling Stories

Entrepreneurs are natural storytellers. But job interviews require a more structured kind of storytelling.

That’s where the STAR method comes in.

STAR stands for:

Situation: What was going on?
Task: What challenge or goal were you facing?
Action: What specific steps did you take?
Result: What was the outcome?

This method helps you clearly demonstrate your value through real-life experiences. And that’s something entrepreneurs have in abundance.

Let’s break it down:

SITUATION: Set the Scene.

“Our customer retention rates were dropping, and we realized our onboarding process wasn’t setting clients up for success.”

TASK: Define the Challenge or Goal.

“I need to redesign the onboarding system to improve retention and create a more seamless client experience.”

ACTION: Describe What You Did.

“I mapped out the existing process, created a new step-by-step welcome journey, and trained my team on delivering it consistently.”

RESULT: Share the Outcome.

“Client retention improved by 35% over the next six months, and support tickets dropped by half.”

Here are a few STAR tips that entrepreneurs can use during the job interview:

Choose diverse stories. Highlight collaborations, problem-solving, and resilience, not just your wins.
Tailor your examples. Connect them directly to the skills the job requires.
Practice out loud. STAR stories are designed to be spoken so they can be remembered.
Stay focused. The structure helps you avoid rambling, a common habit among founders.

Using the STAR method turns your entrepreneurial experience into concise, impressive stories that resonate with hiring managers. It shows that you’re not just experienced; you’re self-aware, coachable, and ready to contribute.

Find the Right Support

Transitioning from entrepreneurship to traditional employment doesn’t just involve a career shift. It’s diving into an identity shift.

And it’s okay to need help navigating it.

That’s why we’re hosting the second session in our Job Searching for Entrepreneurs series: Nailing the Interview: How to Tell Your Story with Confidence.

Whether you’re getting ready for your first interview in years or struggling to translate your founder journey into corporate language, this event is for you. We’ll walk through real examples and hold space for the complexity of this transition without judgment.

This second session is on August 12, 2025, at Offbeat Coffee in Salem, OR. Just like the first session, it will be led by Conrad Rohleder of Clearinity and Malee Ojua of Sacred Fire Creative.

Come as you are – curious, cautious, or completely overwhelmed. You’ll leave with tools, language, and renewed clarity for your next step.

Because you’re not starting over.

You’re starting fresh, with experience, perspective, and something powerful to offer.

RSVP here.