Why Hitting Milestones Doesn't Feel Good Anymore

I am 47 years old. I have a bachelor's degree, an associate's degree, grown children, a career job with benefits, and enough published writing that I stopped counting somewhere in the hundreds.

On paper, I have completed a startling number of the assignments.

So why am I still standing here, bright purple hair and all, trying to build an entirely different life before the one I already built wears me out?

That is not a rhetorical question. Well, not entirely.

I have been thinking about milestones lately, and why reaching one can feel less like crossing a finish line and more like arriving at a rest stop where the bathrooms are locked.

You made it. There is a sign proving you made it. You may even have a little certificate.

You still have to pee.

There was a time when I thought the empty feeling meant I was ungrateful. Maybe I expected too much. Maybe I was one of those people who could never be satisfied. Maybe I had somehow lost my ambition while I was busy completing all the tasks ambition had assigned me.

I don't think that is what happened.

I think I finally noticed that the milestone and the thing it was supposed to give me were not the same thing.

The promise hiding inside the goal

When I became a regular rural mail carrier, it mattered to me. I was proud of it. I had earned a career position, my own route, benefits, and the kind of job people describe as stable.

But there was another promise tucked inside that word.

Stable was supposed to mean I could exhale.

It was supposed to mean I had made it through the uncertain part and arrived somewhere solid. I would work hard, obviously, but the work would build toward safety. The paycheck would make life more manageable. The benefits would protect me. Retirement would exist out there in the distance, waiting like a porch light.

The job was real. The accomplishment was real. I am not taking either of those away from myself.

But my body did not become indestructible when my employment status changed. Bills did not stop rising. One health crisis could still knock the whole careful arrangement sideways. The title changed, but ordinary Tuesday was still ordinary Tuesday, only now I had more to lose if I could not keep doing the work.

That is the part I think we miss when we tell people they should feel proud.

They may be proud.

They may also be looking around for the relief that was supposed to arrive with it.

We were not chasing the diploma

I don't think most of us were ever chasing the diploma, the job title, the house, the promotion, or the follower count just to possess the object itself.

We were chasing what we were told those things would unlock.

Get the degree, and you will have options.

Get the career job, and you will have security.

Get the promotion, and money will get easier.

Buy the house, and nobody can pull the ground out from under you.

Get enough people to notice your work, and opportunity will notice you too.

There was a bargain underneath the whole thing: give us your time, effort, health, attention, and a frankly unreasonable number of passwords, and eventually you will get to feel safe.

I know that bargain never worked equally for everyone. Plenty of people were locked out of it from the beginning. Plenty did everything correctly and were still denied the reward. The supposedly good old days had an extremely selective guest list.

But the bargain was still advertised as if it were universal.

Now more people are reaching the marker and discovering that the promised life is not waiting behind it.

A degree can come with debt and no clear path into the field.

A promotion can come with a modest raise and the expectation that you become reachable at all times.

A house can be deeply meaningful and still bring rising insurance, taxes, repairs, and the unsettling knowledge that the water heater has been making a noise you cannot afford to investigate.

You can do everything that looks like forward motion and still feel as if you have not moved far enough away from danger to rest.

Of course that changes the way achievement feels.

The internet version of a milestone

I have watched this happen in miniature with my writing and social media.

One of my TikTok videos has more than 223,000 views. That is an objectively ridiculous number of people. It is more people than I can picture without turning them into a stadium, and I would prefer not to picture the stadium because apparently my brain finds that stressful.

The video did well.

It did not meaningfully change my follower count. It did not create income. Nobody called with an opportunity. The algorithm did not send a casserole.

For a minute, that made the number feel almost fake.

It wasn't fake. More than 223,000 views is still an accomplishment. What was unreliable was the pile of meaning I had placed on top of it.

I thought being seen by that many people would lead to being remembered by some of them. I thought attention would transfer into readers, followers, work, or at least one interesting email.

Mostly, it meant 223,000 people watched a video and then continued with their lives.

Which is fair. I do that every day.

But it taught me that a metric can be accurate without measuring the thing I actually need.

Views measure views.

A job title measures the job title.

A diploma proves you completed the program.

None of them can promise what happens next.

Sometimes the problem really is exhaustion

There are other reasons accomplishments can feel flat. Depression can drain pleasure from things that would normally matter. Burnout can leave you too tired to celebrate. Sometimes we chase a goal we inherited from our parents, our friends, or a stranger with very white teeth who owns a podcast microphone.

Sometimes the milestone was never ours.

I am not suggesting every disappointing achievement is proof that society has collapsed and we should all go live in the woods. The woods have ticks, and I require plumbing.

I am saying we should inspect the bargain before deciding there is something wrong with the person who feels disappointed.

What was this achievement supposed to provide?

Did it provide that?

If not, is the answer really to chase the next version of the same marker?

That last question is where things get uncomfortable.

It is much easier to assume I need more followers than to ask what I believe more followers will do. It is easier to chase a promotion than to admit what I actually want is more time. It is easier to want the impressive thing than to explain that the life I want might look smaller, quieter, or less legible to everyone else.

The Ordinary Tuesday Test

I have started judging milestones by what I am calling the Ordinary Tuesday Test.

It is basically my Interrogate, Don't Extrapolate rule applied to ambition. The milestone is the fact. "This should finally make me feel secure" is the story attached to it. Sometimes that story is true. Sometimes it was written by somebody trying to sell me the next rung of the ladder.

Forget the announcement. Forget the photograph, the congratulatory comments, and the brief burst of feeling as the number rolls over.

What will be different on an ordinary Tuesday?

Will I have more money after the bills are paid?

Will I have more control over my time?

Will my body be safer?

Will I be doing more work I care about, or only more work?

Will I feel closer to people I love?

Will this make room in my life, or consume the room I have left?

And the slightly mean question: would I still want it if nobody else ever knew I had achieved it?

That does not mean public recognition is shallow. I am a writer. Other people reading the work is part of the job. Money, reach, titles, and credentials can all create real access.

I just want to know whether I am chasing access or applause, because applause is lovely, but it has terrible resale value.

Yes, I am still making a ridiculous bargain with the internet

This may seem like an odd argument for someone currently asking the internet to help her reach one million combined followers and Patreon members by December 31 in exchange for shaving off the bright purple hair she has been building into her identity since 1998. Live. With the Patreon members choosing what the haircut becomes.

I know.

There is a decent chance I have undermined the whole piece.

But that ridiculous public number is the spectacle, not the actual measurement I care about.

The real goal is finding the first 50 people willing to become paying Patreon members so I can begin turning hundreds of published pieces, years of observation, and the way my brain notices people into a sustainable writing career.

Fifty paying readers could change an ordinary Tuesday.

They could buy writing time. They could cover the costs of creating the work. They could prove that the work is useful enough to support itself, even a little. One million followers would look impressive in a headline. Fifty people choosing to help me keep writing would hold actual weight.

That is the difference I am trying to pay attention to now.

Not, "Does this look like success?"

What does this success make possible?

I have not stopped wanting things. Clearly. I am trying to bargain with the entire internet using my hair.

If anything, I have become more ambitious and more suspicious of decorative achievement.

I do not want the next marker simply because it is farther down the road. I want to know where the road goes. I want whatever I build next to buy some combination of time, safety, freedom, connection, usefulness, and fewer Tuesdays spent wondering why doing everything right still feels so precarious.

The milestone can tell me how far I have traveled.

It cannot tell me whether I am headed somewhere I want to live.

That part is still my job.

Want to watch me test this theory in public? Follow Curious Katsouros, or become one of the Founding 50 on Patreon. Apparently I have decided to make the next stage of my career a group project.