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I’ve been grinding for 18 months.
Not the kind of grind that feels productive and energizing, where you’re tired but you can see the finish line. I mean the kind of grind where you’re not sure where the finish line is. The kind where you wake up at 3am and your brain immediately starts doing math you don’t want it to do. The kind where every month that passes feels a little heavier than the last.
When you run your own business, there’s a version of the struggle that you can push through with sheer willpower and optimism. But after a while, the optimism gets harder to manufacture. The bank account tells a different story than the one you keep rehearsing in your head, and eventually, the story the bank account is telling starts to feel more real.
That’s where I was a few months ago when the grind got the best of me.
Welcome to Stuff I Learned Yesterday, this is episode 707, “Grind and Rise.” I’m Darrell Darnell, 58% of Americans prefer pulp in their orange juice, and I believe that if you aren’t learning, you aren’t living.
What about you? Are you a pulp-in, or pulp-free person? I like it either way, but I’d lean toward preferring pulp in my OJ.
My wife and I had built Pro Podcast Solutions, my podcast production and strategy company, over 13 years. And for most of those years, the flexibility the business gave us was everything. We have kids. We needed that flexibility. Working from home, setting our own hours, being present for the stuff that mattered. The business made that possible, and we were grateful.
But the kids are grown now. The season changed. We’re empty nesters, and the things we once needed from the business don’t carry the same weight they used to. And honestly? The things a traditional job could offer — a steady paycheck, health insurance, a 401k — those started looking really, really good. Not because we gave up on the dream. Just because when you’ve been financially strapped and grinding for nearly a year and a half, stability starts to feel less like settling and more like survival.
We’d been intentional about repositioning PPS during this stretch. We made a deliberate pivot to focus on large enterprise clients. Bigger organizations, bigger budgets, bigger engagements. It was the right move strategically, but getting that first big win was taking longer than we’d hoped.
Then a promising client came back into the picture.
I say “came back” because this relationship had already been through a few storms. I’d started working with them the previous fall, spent weeks doing an in-depth evaluation of their podcast network of more than 40 podcasts across four brands. I’d presented my preliminary findings to their executive board of more than a dozen stakeholders. They liked it. They gave me the green light to move forward with the next phase. And then the holidays hit, and when they came back in January, they pulled the plug. Budget freeze. Stop all work immediately.
That stung. I was looking forward to the work, the relationship, and frankly, the income. But then spring came, and so did a message from one of their VPs. My original contact with the company was gone and the VP was reaching out to reengage. They wanted to pick things back up.
I cannot overstate how significant that felt at that moment. We’d been repositioning for exactly this kind of client, and here one was, coming back to us. Coming back to me. I got to work.
Over the next couple of months, I finished the evaluation. I built out my findings and recommendations. I prepped the presentation. And as I was doing all of that, an idea started forming in the back of my mind.
What if they hired me?
Not hired PPS. Hired me. Darrell Darnell. Full-time employee, steady salary, benefits, a place to land. I knew there had been a Director of Content Strategy position within their organization that had been vacated. I knew the VP I’d been working with from our executive meeting the previous fall and I knew she was not permanently taking over the content strategy position. What if that chair was still empty? My wife could take over operations at PPS. I could step into something stable. It made sense on paper. It made sense in my gut. And honestly, the more I thought about it, the more appealing it became.
So I walked into that presentation with two agendas running at once.
I opened by framing my entire approach as if I were already their Director of Content Strategy, sitting in that chair, making decisions as a member of their team. I used “we” language constantly. “We should do this.” “Our best path forward is if we do that.” I planted every seed I could think of, as carefully as I could, without ever just coming out and asking directly. Don’t get me wrong. This strategy wasn’t just self-serving. I also believed that putting myself in that mindset positioned my thought processes to make the best recommendations and evaluations.
The presentation went well. They were engaged. As we wrapped up they asked me to email them the following week with options for how we could work together on implementing my recommendations.
That’s a win. Objectively, that’s a win. That means the relationship continues, more revenue will be coming in, and our ability to serve these levels of clients is validated. But it wasn’t a job offer.
But then I learned that the position I’d been mentally sitting in was already filled. The contact that I’d assumed was the VP’s assistant, had actually been promoted into the exact role I was eyeing. The seat wasn’t empty. The seat had someone in it.
Just like that, the floor dropped out. The version of the story I’d been telling myself for weeks fell apart. And all that was left was the original grind I’d been trying to find a way out of.
I didn’t even feel like I had anything left to grind with. Said differently, I felt like I’d already been ground to a pulp and there was nothing left to grind.
I reached out to my board of advisors. These are the people I trust to tell me the truth even when I don’t want to hear it. I laid out the whole situation. The meeting, the missed opportunity, the exhaustion, the fear. All of it.
And here’s what I learned.
Catherine, one of my advisors, said something that I’d totally missed because I was so stuck in my disappointment. She pointed out that what I had with this company was actually remarkable. Think about it. This client had gone through a budget freeze that killed our project mid-stream. Their primary contact, my original champion inside the company, had left. A new person came in, inherited the situation, and still chose to reengage me personally. And I delivered a presentation that got them asking for more. Catherine called it “trust capital.” She said I had survived every disruption this relationship had thrown at us, and that kind of relationship equity is extraordinarily rare. I had been so fixated on what I didn’t get that I couldn’t see what I had built.
Then James chimed in. With real directness and real compassion, he pointed out that I was making decisions and framing my entire situation from a place of emotional exhaustion rather than sound logic. He wasn’t dismissing the struggle. He was asking me not to let the struggle make permanent decisions. He walked me through what the engagement with the company could actually look like financially if it was priced and structured correctly. The numbers weren’t small. They were, in fact, the kind of numbers that could change the trajectory of the business. I hadn’t done that math because I was too tired to believe the math would be good.
And Sandra? Sandra told me, point blank, that I was underselling what had actually happened in that meeting. The VP had not just been polite. She had not just nodded and said she’d be in touch. She specifically asked me to come back with engagement options. Sandra reminded me that in enterprise sales, that is a warm pipeline opportunity with organizational alignment. She said most consultants would trade almost anything to walk out of a first real meeting with that result. I had walked out of that meeting discouraged, and she was standing there reminding me that what happened was actually good.
I needed all three of those perspectives. Desperately.
Here’s what struck me as I sat with everything they shared: I had blind spots. Big ones. And those blind spots weren’t random. They were the direct result of being worn down. Sixteen months of financial strain, of uncertainty, of waking up at 3am stressed and overwhelmed. That kind of exhaustion doesn’t just affect your body. It rewires the way you see. It filters out the wins. It amplifies the losses. It makes you interpret ambiguous situations in the most discouraging way possible, because that’s the lens that’s been sitting on your face for over a year.
We all get blind spots. But some things make them worse.
Prolonged stress makes them worse. When we’ve been in survival mode for a long time, our brains start looking for threats more than opportunities. We’re scanning for what could go wrong, what already went wrong, what might go wrong next. We stop seeing clearly because we’re too busy bracing.
Exhaustion makes them worse. When you’re tired enough, even good news can feel like a setup. Even a win can be something you squint at suspiciously, waiting for the catch.
Isolation makes them worse. When you’re carrying a heavy situation alone, your perspective becomes the only perspective. And if your perspective is filtered through stress and fear, that’s the only story you get.
What my advisory board did for me was break through all three of those things at once. Catherine gave me a new frame for what I had built. James gave me a new frame for what I was capable of. Sandra gave me a new frame for what had actually happened. None of them were telling me that everything was fine. They were telling me that I couldn’t see the whole picture, and here are the parts you missed.
That’s what trusted people do. They don’t just cheer you on. They show you what you can’t see from where you’re standing.
I think about how often we white-knuckle through hard seasons without ever asking for that kind of help. We convince ourselves that asking means we’re weak, or that we’re burdening people, or that no one really has the bandwidth to care. And we stay in our blind spot. We keep missing the wins that are right in front of us. We keep interpreting decent outcomes as failures because we’re too deep in our own exhaustion to see them clearly.
I’m not saying a good advisory board is a magic fix. The challenges I’ve been navigating are still real. The path forward is still hard. I’m still grinding. But I walked into that conversation feeling like I had nothing left, and I walked out of it reminded that I had more than I thought. A remarkable client relationship. A legitimate enterprise opportunity with significant relationship equity already built. Thirteen years of expertise. A business worth fighting for.
Sometimes the most important thing isn’t getting better information. It’s getting people around you who can help you properly see the information you already have.
Don’t wait until you’re completely ground down to let trusted voices speak into your situation. The bright spots are there. The wins are there. The opportunities are there. You just might need someone standing next to you, pointing.
I’m Darrell Darnell, and this has been Stuff I Learned Yesterday.
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