Five Lessons from a Year in the Grind

There’s no easy button to success. Rome wasn’t built in a day. And neither is the life you want.

Last August, I shared that I had been laid off during a company downsizing (Facing the Unexpected). At the time, I knew I wasn’t the only one. Tech layoffs were everywhere, but knowing that didn’t make the sting any easier.

What I didn’t know then was just how long the rebound would take. A year later, I’ve been through dozens of interviews, countless dead ends, and more moments of doubt than I’d like to admit. I’ve also stumbled into freelancing, storytelling, rediscovered how resilient I can be, and learned some lessons worth sharing.

Here are five reflections from the grind, each one hard-earned.

1. The hiring process is broken

When I first started applying, I went in with optimism. I polished my résumé, updated my LinkedIn, and hit “submit” on every role I was deeply qualified for. Over a hundred applications later, I had exactly one callback. That interview didn’t happen until six months down the line. Two conversations, then silence.

It was like shouting into the void.

The truth is, most of the jobs that turned into real opportunities came from networking. Friends made introductions, former colleagues opened doors, and I found myself in multiple interview funnels. Four times, I made it to the final round. Four times, I was the runner-up.

Each rejection landed like a punch in the gut. I remember one call where the CEO said, “We really liked you, but we’re going in a different direction.” I hung up the phone, sat in silence, and thought, What more could I have done?

But my time in sales taught me something: the deal isn’t done until the contract is signed. You can’t count on a “yes” until you’re holding it in your hands. In today’s tech market, especially for remote roles, the path to that “yes” is narrower than ever.

2. Freelancing is both freedom and exhaustion

After months of chasing roles that weren’t materializing, I started leaning into freelance. At first, it felt like a breath of fresh air. I could choose who I worked with. I could balance multiple projects. I could be my own boss.

But here’s the reality: a freelance day doesn’t look anything like the Instagram version of “working for yourself.” By noon, I’ve often had four calls, one about product strategy for a startup, another about a CRM integration with a company in construction, another about with an offshore engineering team in India, and one more about content. All different clients. All completely unrelated.

By the afternoon, my brain feels like it has been scrambled. Context switching isn’t just tiring. It’s draining in a way I hadn’t anticipated. I used to think, If I can handle this, I can handle anything. Now I know that handling it comes at a cost.

The freedom is real. But so is the exhaustion.

3. Financial realities are humbling

One of the hardest parts of freelancing has been money. Some months, invoices get delayed. Other months, projects wrap up sooner than expected. And then there are months where, no matter how hard I work, the math doesn’t work out.

There were times I had to call my financial advisor and say, “I need to pull money from savings to cover bills.” Every time, I felt like I was admitting defeat. I even told him, “When I have to call you for that, I feel like a failure.”

He reminded me that wasn’t true. This is why you save, he said. So that when life throws you a curveball, you have the margin to handle it.

And he’s right. On paper, using savings in tough times is smart. But emotionally, it’s brutal. It chips away at your confidence. And I know I’m fortunate. Many people don’t even have savings to fall back on. That perspective doesn’t erase the sting, but it keeps me grounded.

4. Starting is easy. Not quitting is hard

Last September, I wrote about persistence in a post called Don’t Ever Give Up. I didn’t realize then how often I’d need to reread my own words.

Starting something new, whether it’s a job search, a side hustle, or freelancing, always carries a spark of excitement. You imagine the possibilities. You dream about where it could lead. The adrenaline keeps you going.

But once the honeymoon wears off, the grind sets in. And it’s the grind that separates those who keep going from those who quit.

There were weeks where I thought, This is it. The breakthrough is here. I’d feel momentum building, only for the opportunity to stall or fall through. It’s like chasing a mirage. Every time you think you’ve reached it, it slips further away.

That’s the moment when quitting looks most appealing. But I’ve learned that’s also the moment you’re closest to breaking through. It’s darkest right before the dawn. This is a marathon not a sprint.

5. Small wins keep you moving.

The encouraging part is this: after months of bleeding, I’ve finally hit break-even. The bills are covered. No more pulling from savings. And I’m working on a project right now that has the potential to put me ahead for the first time in a long time.

Is it glamorous? No. Is it LinkedIn-worthy success? Not yet. But it’s progress.

And I’ve learned to measure progress differently. I don’t look for overnight wins. I look for daily ones. Did I move a project forward today? Did I make something 1% better? Did I push through the hard moments? Those are the wins that compound.

It’s easy to look at others and think they got there overnight. But the truth is, nobody becomes an expert without putting in the reps. Nobody builds a business, a career, or a meaningful life without grinding through the unglamorous middle.

Closing

There’s no easy button to success. Whether you’re chasing a job, starting a business, or simply trying to survive a hard season, the only way forward is through the grind.

Rome wasn’t built in a day. And neither is the life you want.

I’m forging my own path. It’s not traditional, but it’s mine. And that’s something I’m proud of.