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Ever started a new job and realized within hours that you’d made a huge mistake? You’re not alone. From nightmare bosses to sketchy workplaces that looked nothing like the interview promised, plenty of people have noped out after just one day… and honestly, sometimes that’s the smartest move you can make.
Here are a handful of ‘hell naw‘ stories that you may or may not relate to!
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Hendy
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Opinions expressed by Entrepreneur contributors are their own.
I’ll never forget the day I quit my job to pursue my startup full time.
My manager’s office was two floors above mine. The morning I decided to give my notice, I took the stairs. Turns out, two floors is a lot of time to think. Was I making a mistake? Had I lost my mind? My legs felt leaden as I climbed, and by the time I reached the top, my heart was pounding in my chest — and not just because of the stairs.
Making the leap into entrepreneurship will never not be scary. But my manager didn’t give me a hard time about the fact that I was leaving. He asked where I was going, and when I told him about my plans to build my own product, he didn’t sulk, get angry or try to talk me out of it. Quite the opposite: He was excited for me. We shook hands, he wished me luck and he told me I was welcome back any time.
No leader ever wants a good employee to quit. But the truth is, people grow. Their goals change. And if you’ve built the kind of team you’re proud of, you can’t be surprised when someone on it starts to dream bigger. What matters most is how you respond when that moment comes.
That conversation with my manager stuck with me — not just because it gave me the confidence to take a leap, but because it modeled the kind of leader I wanted to be. Years later, when employees started leaving my company, I remembered his reaction. And I made a decision: I would always treat departures with respect, encouragement and an open door.
Because the way you say goodbye says everything about your culture.
Related: What You Should Do If a Valuable Employee Decides to Quit
Founders often see employee departures as threats or betrayals — especially in the early days, when every hire feels critical and every exit feels personal. But that mindset is short-sighted and, frankly, unsustainable.
The truth is, people will leave. Sometimes it’s for a better opportunity. Sometimes it’s for personal reasons. Sometimes they’re just ready for something new. And that’s okay. When I lose a valued employee, I always refer to the wisdom of Don Miguel Ruiz’s The Four Agreements, which I recommend everyone read. In it, Ruiz argues for the value of not taking anything personally: “Nothing other people do is because of you,” he writes. “When we take something personally, we make the assumption that they know what is in our world, and we try to impose our world on their world.”
The opposite of this, which I don’t at all recommend, is burning a bridge out of pride or frustration.
The way you treat someone on their way out sends a clear message to the rest of your team. If you respond with resentment or coldness, you create an atmosphere of fear — one where people are afraid to be honest about their goals, or worse, feel guilty for growing. But if you react with support and kindness, you reinforce a culture of trust, respect and long-term thinking.
Your alumni — yes, alumni — are part of your company’s extended story. They may refer others, return someday or speak publicly about their time with you. That makes their exit just as important as their arrival.
Related: How to Quit Your Job With Confidence and Go All In on Your Side Hustle
Like many aspects of leadership, your mindset matters.
When someone gives notice, respond with curiosity. Ask what they’re excited about — not to challenge their decision, but to understand it. What are they hoping to learn or experience next? These conversations can be enlightening. Personally, they remind me of the ambition and drive that led me to start my own company, and they can offer valuable insights into what motivated employees want from their next chapter.
One thing I’ve learned from running my company for so long is that what looks like a closed door often isn’t. Many of the people who’ve left Jotform have come back, often armed with new skills and expertise that they picked up during their time away. These are called “boomerang employees,” writes Harvard Business Review’s Rebecca Zucker, and they are a critical part of the talent pipeline, both as potential returnees and as ambassadors for future hires: According to Gallup, employees who have a positive exit experience are 2.9 times more likely to recommend their organization to others.
This sort of long-term thinking is the hallmark of a growth mindset. It means believing that careers evolve, people develop and relationships don’t have to end just because a job does. It means choosing encouragement over resentment, curiosity over control.
And most importantly, it means seeing every departure not as a loss, but as a sign that you’re hiring and leading the kind of people who are always striving for more. That’s something to be proud of.
I’ll never forget the day I quit my job to pursue my startup full time.
My manager’s office was two floors above mine. The morning I decided to give my notice, I took the stairs. Turns out, two floors is a lot of time to think. Was I making a mistake? Had I lost my mind? My legs felt leaden as I climbed, and by the time I reached the top, my heart was pounding in my chest — and not just because of the stairs.
Making the leap into entrepreneurship will never not be scary. But my manager didn’t give me a hard time about the fact that I was leaving. He asked where I was going, and when I told him about my plans to build my own product, he didn’t sulk, get angry or try to talk me out of it. Quite the opposite: He was excited for me. We shook hands, he wished me luck and he told me I was welcome back any time.
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Aytekin Tank
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What happens when everything you’ve built stops feeling like you? How do you get the courage to scale down?
This isn’t a story about burnout or business failure—it’s about the radical courage to honor who you’re becoming, even when it makes zero logical sense.
In this episode, Meghan shares why she walked away from a globally successful business that was thriving by every metric. The real moment she knew. The price tag of freedom. And the terrifying question every successful person faces: “Who am I without this?”
If you’ve ever felt disconnected from something you worked hard to build, wondered if you’re allowed to want something different, or questioned whether success is supposed to feel this heavy—this conversation will hit different.
Because sometimes the most courageous pivot isn’t growing bigger. It’s trusting the whisper that says it’s time to scale down and come home to yourself.
Perfect for anyone ready to redefine what success actually means.
In this episode, you’ll discover:
Subscribe and listen to The Courageous Pivot Podcast on:
If you’re loving the show, please be sure to leave a review!
00:00 Welcome to the Courageous Pivot Podcast
00:27 A Day in the Life Post-Pivot
03:19 The Joys of Scaling Down
04:28 The Whispers of Change
06:11 My Journey to Empowerment
09:51 The Reality of Success
11:08 The Decision to Pause
14:31 Embracing the Unknown
16:28 Reflecting on the Pivot
19:18 Final Thoughts and Next Steps
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Meghan Telpner
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It would have made sense for Hardy to tone down his first-ever set at Rodeo Houston on Saturday night. Family crowd. Country venue. Corporate environment. Some even predicted as much (good job by me).
Hardy doesn’t roll that way. And that’s what makes him one of the hottest, most unique artists in the country scene today.
The opening Saturday is always a big slot, and Hardy more than delivered, blaring through a 14-song, hour-long set that was long on rock and short on subtlety.
He kicked the set off with two rockers – “Sold Out” and “Kill Sh!t Till I Die.” He mostly refrained from profanity, though he certainly encouraged the crowd to pick up the slack on that end. His band sounded more 90s rock than 90s country.
Yeah, it was that kind of show.
Of course, anyone who considers themselves a true Hardy fan shouldn’t have been surprised. The man has made no secret of his affinity for genres outside the traditional country box – namely, rock and hip-hop – and both were on display in full force on Saturday night via tracks like “Rockstar” and the show-closing “Quit!!”
That said, Hardy at his core remains a true country artist, so he certainly made room for more Rodeo-friendly music. “Wait in the Truck,” with Lainey Wilson piped in on the video board, really drew a response. The poignant “Give Heaven Some Hell” had some folks on the video board crying and singing along simultaneously. And “God’s Country,’ which Hardy wrote and Blake Shelton (who opened this year’s Rodeo) originally performed, really engaged the crowd.
The show probably peaked when Hardy sang “Boots,” “Truck Bed” and “Unapologetically Country as Hell” in succession, if only because those are three of his catchiest and most known, accessible songs. If any songwriter in the game today knows how to craft a hook, it’s Hardy.
By the time Hardy jumped in the back of a Ford pickup truck for the customary ride out, many in the crowd were ready for more. Hardy more than made the most of his first trip to Rodeo Houston. Here’s hoping it’s the first of many.
Set List
Sold Out
Kill Sh!t Till I Die
Jack
Boots
Truck Bed
Unapologetically Country as Hell
Rockstar
One Beer
Wait in the Truck
.30-06
Give Heaven Some Hell
Rednecker
God’s Country
Quit!!
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Clint Hale
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Opinions expressed by Entrepreneur contributors are their own.
I’m a great loser. Before I explain just how good I am at it — and why you should work at it, too — you need to know two things about me:
First, I’m a day trader. Much of the investing world values the long-term “buy and hold” strategy. Warren Buffett is the most famous example, and he’s done well. In contrast, the very definition of day trading is that you cannot hold any positions overnight. In my case, I rarely hold trades for even hours. My average hold time over my last 20,000 trades has been about five minutes.
The second thing to know is I’ve built both my day trading account and my information business by self-funding them. Much of the business world values leverage. It’s the notion that if you really believe in your business, you should take on debt or get equity partners. “You’re either growing or you’re dying!”
Being a day trader and a self-funded business owner have combined to make me really good at cutting my losses. Here are four principles for cutting losses that may be useful to you, even if you have no intention of day trading.
Related: I Turned $583 into $10 Million. Here’s How I Did It and 5 Lessons I Learned Along the Way
Currently, I could afford to lose six figures in a trade, but instead, I still trade the same way I did when my back was against the wall.
For a little backstory, I lost a lot of money day trading until I was close to broke: I was divorced, living with my dog in Vermont, selling my furniture on Craigslist and chopping wood instead of paying for heat. In that crucible, I identified what my previous winning trades looked like and one other thing: that I was holding my losers too long. I had to cut my losses faster if I would survive.
This is painful to do! Walking away not only removes the hope that the situation may turn around, but it goes against what we’ve all been told: “Stick with it! Don’t be a quitter! Finish the job!”
Let’s say your situation is different: you have enough money that you can stick with a difficult situation for a while. Should you?
I don’t know your situation, but I do know this: making the decision to quit is doubly hard when you’re in the thick of it. The best way to decide is to identify your quitting criteria upfront. In day-trading lingo, it’s your “max loss.” You are insane to take a position in a stock without knowing the point at which you absolutely must sell. That way, you don’t need to think or evaluate if that number is reached — you simply must react. If you know those criteria with the business venture you’re involved in, it will be far easier to minimize the pain if things suddenly go south for you.
Related: Stepping Aside: When To Walk Away As A Leader
A “sunk cost” is what you’ve already spent on a project at the point when you start to think about abandoning it. Examples might be a half-built nuclear reactor, a Pentagon project wallowing in budget over-runs — or the project that’s become a boat anchor to your business.
You might already have spent a lot on that project, and writing it off may be painful and embarrassing, especially if only recently you were on record as optimistic. The only thing worse would be to throw even more good money after bad. You need to be willing to cut your losses.
Here’s how it happened to me. Day traders can — and should — use a trading simulator to develop and test their trading skills without risking real money. It’s a crucial piece of software, so we decided to buy some source code to form the basis of our proprietary simulator. We customized it, and it worked quite well.
Only it didn’t scale. The first 50 to 100 users liked it, but the system began to show signs of choking with hundreds of users. I had invested six figures in buying and modifying the code. Could we have rebuilt it from the ground up? Yes. But the prospect of turning it around was too far distant. I threw it away and entered a partnership with a company that specialized in simulation software. That hurt, but it was the right move.
Business owners want engaged employees who feel their opinions are being listened to. Sometimes, that means doing the opposite when it’s in the company’s best interest.
There have been times when I had gut intuitions about what we needed to do, and my team was like: “This is way too much! How are we even going to explain this when people write in?” In these cases, I tell them: “I have confidence that you’re going to figure it out.” My job is to solve what will work long term, and other team members must solve the challenges in their areas.
Related: How Business Leaders Can Keep Employees Engaged
When you don’t cut your losses quickly, that’s an opportunity cost: you’ve spent time managing the loser when you could have redirected that time and money to other opportunities. But an extended loss has another downside: it shakes your confidence for weeks or even longer. In contrast, a quick decision to cut a loss can be a confidence builder.
Making decisions is like exercising a muscle. Some decisions are easy, like where to eat. But when faced with a tough one involving losses, consider using that muscle, feeling the pain, and doing it anyway. You’ll be that much stronger.
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Ross Cameron
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