I am 53, and I Don’t Know What I Want to Do When I Grow Up

Indecision and a life surviving pain has left me with only questions I must answer before I move on

Jason Weiland
4 min readMar 26, 2021


Photo by Annie Spratt on Unsplash

“You are a frustrating man because, in some ways, you are mature and level-headed — a good father, husband, and a caring and generous human being. In other ways, you are like a teenager, not knowing what you want to do with your life and dragging your family through one failed scheme after another. I wish you would grow up!”my wife

It’s no secret that unconventional people take the road less traveled. We know we are different, and instead of having shame about who we are, we embrace it.

I’ve spent my entire life looking for a purpose. I’ve searched in books, in people, in drugs and alcohol. I’ve reinvented myself hundreds of times. I’ve started businesses, projects, friendships, marriages, and partnerships, only to figure out that I didn’t want what I thought I did.

I’ve spent my life in low places — in deep depressions and psychotic episodes that felt like they would never end. I’ve sat in darkness in my mind for months, numbed by pain and too many prescription medications.

I’ve lived lifetimes in daydreams and flights of fancy because I felt my real life didn’t measure up to the visions in my mind. I’ve fallen in love with the phantoms who speak to me from the darkness in the back of my head.

Sometimes the demons make better companions than real people.

All the daydreams and hoping for a better life made it hard for me to make decisions, and when I did finally choose, I hated what remained.

I’ve had a hundred different jobs and a hundred more career paths that I thought I would like to try, and a list of failures as long as the line of ships waiting to get through the Suez canal.

So I took my own path, did what I had to do to survive, and promised myself that one day I would finally find the thing that would give my life purpose.

Along the way, I helped build families on both sides of the globe. When I got older, I embraced a new marriage and two more beautiful kids to fill my heart with joy. Being a father and husband is the most important and rewarding job I’ve ever had, and it’s brought me a lot of joy.

But still, I find myself searching.

Even though my heart is full, there is a part of me who keeps saying I am special, and my life has some grand purpose. I still feel like there are things I should be doing before I die a happy older man.

So here I am, in my 50s and still trying to figure things out. I still haven’t decided how to earn money to feed my family, and I haven’t guessed the best outlet for my creative energy. I don’t have a plan for the next ten years and don’t intend to make one because the only times in my life where everything worked out, I didn’t set goals and went with the flow.

I have much I want to try — podcasting, video, books, travel writing. I have issues that I want to improve about myself, and I have things I want to learn before I get too old and unmotivated.

I have a lot of living left to do, and it’s time I get started.

I will admit that the pandemic threw a wrench in my progress and slowed me down in some aspects. I had intended to do a bit of solo travel, but now that everything has changed, I no longer want to sit in a metal tube 30K feet in the air, surrounded by plague rats and anti-maskers.

There are still some loose ends in my life that I left when I moved to the Philippines, and eventually, I will have to go back to a place that feels foreign to me and make things right. I don’t know where my home will be in five years, but at least I know my family will be with me.

It’s time to start thinking about my children’s future as well. How much has COVID-19 changed about higher education and the future of work? What will our everyday reality look like after realizing that we were never safe and secure?

How will my kids live in a world where the climate is trying to get payback for all those years of abuse? Will capitalism fall and fail, and how will my kids work, put a roof over their heads, and survive a future that looks increasingly bleak.

I may have spent my life looking for a purpose only to find I don’t have any time left. Perhaps I’d had too many chances, and I used them up trying to get through the dark days alive and whole.

What if all the good years are already behind me?

I need to believe that I will find what I’m looking for someday and that my journey hasn’t been in vain. I need to grow up and figure out what I will do with the rest of my life before it’s too late and I can’t get anything done I set out to do in life.

It’s time I stopped acting like a scared teenager and did something with the time I have left.

Life isn’t all about the constant search for meaning. Sometimes you have to grab on to something and hold on for dear life.

The future does not favor the timid; so it’s time I finally started acting like the man I am.



Jason Weiland

Personal essays and articles from a guy who never tires of writing about his life - jasonweiland.substack.com