My Second Mid-Life Crisis
Over 6 years ago, I separated from my then wife, choosing to live a separate path—albeit an overlapping path as we co-parent our two boys. This was my first crisis. Now, years later, I find myself struggling with something different.
Growing up, seeing what those around me did, I saw a familiar pattern: you work hard and consistently until your 60s and hope to have enough saved up to support you through retirement. This is what I’ve seen my mom do. It’s what I’ve seen my friends’ parents do. It’s what I see my friends doing now.
Of course, along the way, there are hiccups. Little hills and valleys. The hills are exciting as a sudden influx of cash eases the burden; the valleys are distressing as I struggle to make ends meet.
Working freelance had lots of peaks and valleys but, at the time, I was married and the second income helped smooth the edges out. It made things manageable.
Some say divorce is the easy way out but I didn’t find it particular easy. The emotional and financial cost grew quickly. But it was the only way I could think of to get to somewhere better.
Guilt and other factors from the divorce put me in a difficult place financially. Despite a recently acquired full-time job that paid well, I still struggled to make ends meet. I was paying half a mortgage on a place I didn’t live in, rent for my own place, and child support.
I was on the verge of bankruptcy.
It was a weird place to find myself. I was getting paid over $100k a year and struggling to make ends meet. I made it through that deep trough, in no small part thanks to the help of my mom and Kitt.
From there, it was a slow climb out. I divested myself of any savings I had, refinanced, and built a plan to get out of debt. At my worst, I was $60k in debt and no assets. I didn’t own a house, I was leasing a car, and my budget was at its limit.
Things began to ease up. I moved into a cheaper place. Daycare costs dropped as the boys went on to school. And more room in my budget opened up as debt was paid off.
At the same time, my career began to speed up. A job at Yahoo!, writing a successful book, working at Shopify, and the numerous conferences and workshops amongst it all.
I bought a car and was able to put a down payment on a nice house. I have savings and investments and the real possibility of retiring early—for whatever retiring actually means.
And it is here that I’ve found myself in the middle of my next personal crisis. I am successful. That thing that we work hard to get to has been attained. And I find myself asking “what’s next?” What is that next goal I should be working towards? What will push me to be excited to get up in the morning?
It’s not just money. It’s also interest. That which filled me with excitement has become routine.
I feel like I’m in a holding pattern waiting for the universe to present an answer at my feet. Realistically, I know that’s unlikely to happen. My crisis is requiring a bit more soul-searching. It will take some time, yet, to get my momentum back.
But damn if I don’t just want to buy a red convertible and drive off into the sunset.