Articles Tagged with: job searching for entrepreneurs

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.

How to Talk to Your Family About Money as an Entrepreneur

Starting a business is about chasing a dream – more freedom, more purpose, more control over your future.

But what many entrepreneurs don’t anticipate is how quickly that dream can stir up tension or confusion at home.

You might find yourself avoiding certain topics around the dinner table. You might downplay a rough month or overexplain a business expense.

Or maybe you just carry the weight quietly, hoping your loved ones will understand eventually.

But here’s the truth: your family doesn’t need perfection when it comes to money matters.

They need communication.

Why Is It Important to Talk to Your Family About Money?

Money is deeply personal. It’s tied to security, identity, culture, and even love. And when you become an entrepreneur, your relationship with money often changes. Sometimes, the changes can be dramatic.

Your income may fluctuate. Your expenses may increase. Your financial priorities may shift from steady paychecks to long-term investments and high-risk decisions.

And yet, many entrepreneurs try to shoulder these changes alone, believing they’ll protect their loved ones by staying silent.

Unfortunately, silence creates distance.

When your family doesn’t understand your financial reality, they can’t support you through it. Talking openly about money helps bridge the gap between your business goals and your personal life. In turn, it allows you to build stronger and more resilient relationships in the process.

Opening Up About Money Can Be Beneficial for Your Relationships

Bringing your family into financial conversations isn’t just a responsible move. It’s a move that can strengthen your relationships.

Here’s what happens when you choose openness over avoidance:

You build trust and reduce anxiety.

When you’re quiet about money, your family is often left to fill in the blanks. And most people assume the worst. Talking things through can bring a sense of calm. It tells your loved ones, “I respect you enough to be honest,” even when things are uncertain. That trust is foundational, especially during times when your business is still growing.

You set clear expectations.

Family members may not understand what being “self-employed” really means. By explaining what to expect, like why your income might be higher one month and lower the next, you create alignment and avoid misunderstandings. Clarity helps everyone plan better together.

You invite emotional and practical support.

You don’t need to carry everything on your own. When your family understands what you’re navigating, they can offer meaningful help, whether that’s encouragement during a slow month or flexibility when your schedule gets hectic. Sometimes, the greatest relief is just being seen.

You lay the groundwork for future conversations about wealth and legacy.

If you have children, or plan to have them, how you talk about money will shape their financial future with it. Including your family in financial conversations helps break generational silence and opens up opportunities to co-create long-term visions about shared wealth, values, and impact.

It’s True: Talking About Money Can Be Hard

If talking to family about money were easy, more people would do it. But this kind of conversation can feel deeply vulnerable and fraught with unspoken history.

Here are some of the emotional and logistical hurdles you might face:

Fear of judgment

You may worry that your money won’t understand your choices. Or worse, they’ll see your financial ups and downs as personal failures. This fear can be especially strong if your family values traditional career paths or stable income.

Guilt over taking risks

Many entrepreneurs wrestle with guilt, especially if loved ones have sacrificed to support them. You might feel like you’re letting people down by not being “further along” or by choosing a path that feels uncertain to others.

Power dynamics and past experiences

In some families, conversations about money are tangled up with financial control, inequality, or trauma. You might feel like you’re not “allowed” to lead a money conversation or that speaking up will spark conflict.

Communication gaps

Not everyone speaks the language of business. When you start explaining profit margins or investment timelines, eyes may glaze over. It’s easy to feel discouraged if your family doesn’t seem to “get it.” But that doesn’t mean the conversation isn’t worth having.

These challenges are valid. But they’re also navigable, though it takes care, courage, and the right tools.

How Can You Start the Money Talk?

If you’re ready to open up but aren’t sure where to begin, here are a few ways to ease into it:

Lead with honesty and vulnerability.

Start small. You don’t need a spreadsheet or a formal agenda. All you need is a willingness to say, “I’ve been thinking a lot about how money impacts all of us, and I’d like to talk about it.”

Share your “why.”

Help your family understand the bigger picture behind your business decisions. When they see what you’re building and why it matters to you, they’re more likely to offer support, even if they don’t fully understand the details.

Be clear about what’s changing.

Are you adjusting household budgets? Pausing vacations? Reinvesting income into the business? Lay it out with compassion and transparency so everyone knows what to expect.

Invite dialogue, not just approval.

Let your family ask questions or express concerns without feeling shut down. The goal isn’t to convince them you’re right. It’s to foster mutual understanding.

Make it a habit, not a one-time talk.

Talking about money once is brave. Making it a normal part of your day-to-day is transformative. Schedule regular check-ins. Use tools, books, or resources to guide the conversations. Keep it going.

It’s not easy to talk about money, even with the people you love. But with the right mindset, tools, and intentions, you can start the conversation, keep it going, and make it a way to strengthen your relationship with your family.

Want a Safe Space to Explore These Conversations?

If you’re in the McMinnville, Oregon area, you’re invited to join us at “Money Club: Take Control of Your Finances, One Conversation at a Time.” This is an in-person conversation about money facilitated by financial educator Kristen Winter and founder resource connector Malee Ojua.

Each month, we gather entrepreneurs, creatives, and changemakers in a safe, heart-centered space to talk about the emotional side of money. This August 14, 2025, we’re diving deep into how to talk about your family about money. Because business is personal, and the people closest to us deserve to be part of the journey.

This is an opportunity to hear real stories from your fellow entrepreneurs, gain new tools to start or deepen the money conversation, and find a sense of relief that you don’t have to figure this out alone.

Click here to RSVP and join us in changing the way we talk about money, starting at home

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Job Searching for Entrepreneurs: Reclaiming Your Story, One Résumé at a Time

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.