Why Don’t I Feel Good Enough?

The guilt gap between rest and action

Vaibhav Gupta
4 min readOct 12, 2022
Photo by Riccardo Mion on Unsplash

6th July 2019 was a pivotal day in my life, and it’s because I didn’t do a single thing that day.

My first job out of college was with a Fortune 100 company as a completely average tech writer, and I hated that job. I hated the way I felt, but never had the courage to quit. I felt like I wasn’t good enough to find another job. I stuck around for 5 years.

Thankfully, the decision was made for me in March 2019 when I got laid off.

Within two months I had found another job at a much smaller company where I was the only writer. I started on the 20th of May. I was also elected as a ‘Division Director’ in Toastmasters International on the 24th of May.

In one fell swoop, all the insecurity was shattered. This was my shot. In a matter of months, I was in a completely new space.

I felt good, responsible, and ready — determined to not feel mediocre like I did at my previous job. My Division Director role was due to start on July 1st and at the day job, I was re-creating all their developer documentation from scratch. Suddenly, I was working more than ever and loving it.

However, I remember feeling extremely overwhelmed on the night of the 5th of July, Friday. The first week of July, I had put in over 80 hours across the day job and Toastmasters.

I remember thinking to myself, “is this what the rest of the year is going to be like?”

That night, I had a revolutionary idea — I was going to take the next day off. I decided I wasn’t going to do anything that day.

You don’t need to earn a holiday — you should just take one.

And I did exactly that. I stayed home, and delegated any work that came in. It was my day off, and for the first time ever, I didn’t feel guilty. I felt like I had done enough work to earn that day off.

The next day, I woke up feeling like I’d taken a 2-week vacation.

What happened?

A day off is not a revolutionary concept. It’s in the literal Bible — even God took a day off. But apparently God isn’t good enough for my generation, the millennials, because we try to work all the time.

My generation was bred to win the system, to work hard to succeed and work harder if we cannot see the success. Sleep, meals, and basic healthcare all take a backseat while we proudly brandish the tattoo of “hustle” seared into our skin from the start. It’s a badge of pride to work more than others.

But your body doesn’t work that way. If it’s not maintained and taken care of, it will break down.

I had been burned out for a long time. I just didn’t know it then.

So why was the 6th of July different? It’s because I felt like I had EARNED that holiday. I had been working so hard that I overloaded the part of my brain that thinks I need to work all the time, and could only think about food, sleep, and health.

How do you “earn” a holiday, and why do you need to?

You don’t need to earn a holiday — you should just take one.

However, that goes against the programming we’ve grown up with. We’ve been told time and again that the way to “win” is to work. Any deviation from that leads to a feeling of guilt that we’re not being everything we’re supposed to be.

It’s a very terrifying divide between body and mind. The body needs rest, but the mind feels guilt and tries to push the lagging mule.

On 6th of July, 2019, I had a meeting to possibly save a Toastmasters club in my division that was dying. I delegated it to one of my team members, and we ended up losing that club. It put us behind the 8-ball for the rest of the year, but that day I couldn’t do anything. So I took a day off without guilt.

Guilt is a tool, not a weapon.

If you struggle with any level of anxiety, this is an important lesson to remember. Guilt can be good when it is healthy. Healthy guilt helps us acknowledge mistakes and be better in the future.

But for anxious people, guilt is a poison consumed in excess. Taking time off, enforcing your boundaries, giving yourself space are all privileges we don’t think we deserve; we just need to work harder.

The decisions you make with your life are yours. And with most decisions of any relevant value, you have some skin in the game. There is a risk of losing out on an opportunity to return. There’s an economics term for this — opportunity cost.

For the anxious person, opportunity cost is a good thing — it’s a sobering reminder that you cannot do everything on your own, and rest is something you need to make time for.

You’re not a terrible person if you rest, or if you take care of yourself. Yes, you could always be doing something else, but sometimes you don’t want to, and that is okay.



Vaibhav Gupta

Professional technical writer, 2x Distinguished Toastmaster. I write about mental health and self-awareness. Also see https://medium.com/thorough-and-unkempt