February 21, 2026

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Last weekend, my wife, Jennifer and I walked into our favorite local restaurant for Valentine's Day dinner. We’d planned on cooking at home, but we had a lazy change of heart at the last minute. So we felt lucky to squeeze into two seats at the bar without a reservation.

But when the bartender handed us menus, it wasn't what we expected. We love this restaurant for specific dishes, and they were only offering a prix fixe menu that night (our dishes were not included). Four courses, pre-selected, no substitutions.

I wasn’t feeling it, and I suggested we move along and find something else.

We knew it would be difficult to find another place on Valentine’s Day without a reservation. The town was bustling, and it felt awkward to reject the menu. The bartender had already poured water and set us up for a meal. I definitely felt the pull to simply be nice and stay put.

But instead, I said, "I'm not feeling this menu. I think I'm going to pass."

And guess what?

We walked down the street and scored two bar seats at another restaurant we’ve been wanting to try, and ended up having a wonderful dinner.

But not long ago, I wouldn’t have had the courage to get up and leave. I would have sat down, had whatever was offered, and complained about it the whole way home.

I’ve spent most of my life doing that.

My six months at Salesforce

Back in 2013, I was getting ready to leave Zocdoc, the first job I ever loved. A good friend’s girlfriend was a recruiter at Salesforce in New York City, and they had an open sales position that seemed like a good fit.

I'd heard all the stories about Salesforce reps making great money, getting world-class training, and loving the job. So I asked her to help me get an interview. She hooked me up, and I got the job.

But when I showed up for training, it didn’t feel right on the very first day.

The product wasn’t exciting. And I didn't like the rules and processes the sales team had to follow. I’d just come from a fast-growing, wild-west kind of startup where I asked for forgiveness instead of permission. And now I was sitting next to my boss's cubicle all day, making scripted cold calls to IT people. It was suffocating.

I knew in the first two weeks it definitely wasn't right. But I told myself to give it time. Eventually, it would click. This was just an adjustment period. And more than anything, my friend's girlfriend had gone out of her way to help me get this job. Quitting would make her look bad, make my friend mad, and I’d look like someone who couldn't stick with anything.

So I kept showing up. Every morning, I took a terrible two-train commute from Brooklyn to the office, trying to convince myself things would get better. And weeks turned into months. Once in a while, I'd have a decent day, just enough to talk myself into staying a little longer.

But I never once woke up excited to go to work. Not a single day in six months.

I finally quit after half a year. My friend's girlfriend was mad at me. He was pissed. My boss thought I’d wasted everyone’s time. And, of course, I felt terrible about all of it.

But I’ll tell you something. Looking back on all of this, the thing that bothers me the most is that I knew right away. I had all the information, yet I spent six months enduring something I knew was wrong. Because leaving felt harder than staying.

Not long after I quit that job, I landed the VP of Sales role at PatientPop. PatientPop was thrilling from day one. I clicked with the team, and I loved the product. And over the next four and a half years, we built that company to over $70 million in revenue. That job was a perfect fit for me, and we had a lot of success because of that.

None of that happens if I'm still sitting in a cubicle at Salesforce, cold-calling IT departments. And it almost didn't happen, because I nearly talked myself into month seven.

What Jennifer figured out before me

I've watched Jennifer handle all kinds of weird situations she didn’t like over the years. And what always strikes me is how naturally the option occurs to her. The option to just stop.

Several years ago, for my 40th birthday, we decided to invest in something special for the big milestone and booked a few nights at a luxury resort in Vermont. It’s a once-in-a-lifetime kind of place to visit, and we were pinching ourselves from the start.

Throwing all financial cares to the wind, we added massages to our activity plans. I usually get massages at a cheap place in my little town shopping center, so the price of these massages was a sticker shock. But we were there celebrating, so we booked them anyway.

My massage was everything I expected, and I floated out of the room in my robe feeling like a brand new person. But when I got back to the waiting area, the receptionist told me Jennifer had left her treatment early and would meet me back at our cabin.

It turned out that Jennifer’s experience was nothing like mine. Her therapist didn’t seem to know what she was doing, and she wasn’t prepared for the treatment as the time started ticking. She shuffled in and out of the room several times, and when she finally started the massage, she prompted Jennifer for small talk.

Jennifer knew in the first ten minutes that she didn’t want to continue. So she told the massage therapist it wasn’t working for her and that she wanted to stop. She got up, got dressed, and left.

When Jennifer told me what happened, I felt embarrassed at first.

I thought she should have just gone through with the treatment. We were at this amazing place, the staff had been so nice, and I didn’t want them to think we were difficult.

But Jennifer saw things a different way.

We were at this amazing place. And we were paying for it. Clearly, the resort had high standards, and her experience wasn’t appropriate for the cost or for the setting. Some baseline training was obviously missing, and that didn’t match the price.

And she was right.

When Jennifer knows something is wrong for her, she doesn't run through all the reasons she should endure it anyway, or carry on a lengthy internal debate. The option to exit is obvious to her in a way it never was for me.

And what I’ve come to learn about situations like this, where you feel stuck, is that the consequences are usually much different than what we conjure up in our worried minds. For some reason, we don’t imagine taking control of a situation and it working out for the best.

Turns out the spa was short-staffed that day, and the resort manager was mortified that a substitute therapist had not met their standards. They did backflips to make up for Jennifer’s bad experience and comped her treatment. The Valentine’s restaurant squeezed two other people into the bar after us. And my friend’s girlfriend (now wife) has long forgotten my quitting. We’re all still friends, and it’s ancient history.

The bottom line

I spent six months at a job I knew wasn't right for me. I would have laid on that massage table for the full hour. And I would have eaten the Valentine's Day meal I didn't want. For most of my life, "making the best of it" was my default setting.

That’s most of us, I think.

Jennifer has shown me that there's always another option, and a lot of the time, great things can happen after you take the uncomfortable steps of saying, “This isn’t for me. I’m outta here.”

You really can just stop something that isn’t working for you. You can be polite and straightforward and walk away.

The restaurant last week was a small moment. But it was proof that something has changed for me.

So here's my question for you today:

What's something you've been enduring that you know isn't right? And what would it take for you to finally say "stop"?

Reply and tell me. While I can't reply to everyone, Jennifer and I read every response, and we love hearing from you.

That's all for this week.

See you next Saturday.

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