Am I Climbing the Right Ladder?

Sunday, April 26, 2026 — A stream of conscious journal entry on the way to work

By Justin Stephens | justindcstephens.com

This morning I dropped my kids off at their mother's house, pointed my car toward WinCo, and started talking to my camera glasses. No script. No plan. Just me, the road, and whatever was on my mind.

That's what this blog is. My life, unfiltered, in real time. I'm a Boise, Idaho entrepreneur and content creator documenting the journey of building a personal brand, a business, and a future — one honest day at a time.

So here's what's been on my mind.

Am I Climbing the Right Ladder?

There's a question I keep coming back to lately: Am I climbing the right ladder?

It's one of the most important questions anyone building a career can ask themselves. Because you can work incredibly hard, stay incredibly consistent, and still end up at the top of the wrong building.

I love my job at WinCo. Genuinely. I love the business model, the ESOP structure, the way they take care of their people. I love walking into that store and knowing I'm an employee, an owner, and a customer all at once. That means something to me.

But I'd be lying if I said the financial reality wasn't hitting hard right now.

The honest truth is I'm struggling. Between child support and the cost of rebuilding your life from scratch, I'm barely keeping my head above water. Some weeks it doesn't even feel like above water — it feels like treading, just trying not to go under.

My parents have been incredible through this season. Without their support I genuinely don't know where I'd be. I feel blessed to have them. I also hate needing to ask for help. Both things are true at the same time.

So the question I'm wrestling with is real: Do I stay at WinCo, grow within the organization, keep chasing the buyer role I want, and trust that the long game pays off? Or do I take my skills somewhere that pays me what I'm worth right now and get myself back on my feet faster?

This is what it actually looks like to know if you're on the right path — you keep asking the hard questions honestly, even when you don't have the answers yet.

I don't have the answer yet. But I'm asking the question, and I think that matters.

The Dating Thing

I'll throw this in because it's real and it's been on my mind too.

I'm good at settling. Like, really good at it. I can find contentment almost anywhere, with almost anyone. On the surface that sounds like a virtue. But I've been asking myself lately — is it actually holding me back?

What I want in a relationship is pretty clear. A woman who has her own dreams and wants to support mine. Someone I genuinely want to spend time with who wants to spend time with me. I'm open to being a stepfather — I think that would be a privilege, honestly.

But here's the other side of it: life without a relationship right now is easy. I make my own decisions. I move at my own pace. My freedom, limited as it is by a tight budget, is still mine.

Do I want a relationship? Yes. A hundred percent. But I'm also being honest with myself about the timing and what I actually have to offer right now. That's not pessimism. That's just self-awareness.

For any single dad building a future out there — I think you know exactly what I mean.

What Dreams Are Actually For

Here's something I've been thinking about a lot that I want to share with you.

Most people think the point of a dream is to achieve it. I don't believe that anymore.

I think the point of a dream is to give you somewhere to walk toward.

Whether I end up as a buyer at WinCo, on their board of directors, running America's Holding Company, or representing Idaho in the House — I genuinely don't know if any of it happens exactly the way I picture it. I could fail epically. I could fall completely flat on my face.

And I'm okay with that.

Because here's what I know about defining success on your own terms: the version of me who is actively chasing something is a better version of me than the one who isn't. The journey changes you. The attempt changes you. Success, to me, isn't the destination — it's waking up every single day and choosing to move toward something that matters to you.

If my current dreams don't work out, I'll dream new dreams. That's not giving up. That's just life.

What I'm Building and Why

Let me be clear about the strategy, because I think it's worth explaining.

Building a personal brand for the long term — this blog, the social media content, the videos, all of it — is not just content for content's sake. It's the foundation of everything I'm trying to build.

The political future. The AHC vision. The WinCo journey. They all run through trust. And trust is built over time, through consistency, through showing up, through being real with people even when it's uncomfortable.

That's why I post every day. That's why I use my camera glasses to capture first person footage at work. That's why I'm writing this blog entry about financial struggle and ambition instead of pretending everything is fine.

I'm not performing a life. I'm documenting one.

And I believe — I genuinely believe — that if you show up honestly for long enough, the right people find you. The right opportunities find you. The trust you've built becomes the most valuable asset you have.

In politics, in business, in life — trust is the currency that matters most.

A Word on Ambition

I'll end with something I said out loud in the car this morning that surprised even me.

"I hope you don't have as ambitious dreams as I do. Because it's incredibly lonely having ambitious dreams."

I meant it. When you're at the beginning — before you've proven anything — people won't believe you. They can't. Belief has to be earned. And in the meantime you carry the weight of the vision mostly alone.

But here's why I push toward ambitious dreams anyway, especially when it comes to chasing your dreams when life is hard:

If I aim at the extreme and you meet me halfway, you've still done something remarkable. If I aim small and you meet me halfway, we've both wasted the opportunity.

So I aim big. Not to be reckless, but because I believe the people following this journey deserve someone who is genuinely trying to do something extraordinary. Even if extraordinary takes years. Even if it looks like stocking shelves in a WinCo uniform on the way there.

What dreams are you chasing right now?

What would they write on your gravestone — and would you be happy with it?

If not, now is the time to change. Don't wait. Life is fleeting and it's yours to write.

Chase your dreams. I'll be right here chasing mine.

— Justin Stephens | justindcstephens.com

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