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.

Published October 04, 2015
Categorized as Personal
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Peter Wilson said on October 04, 2015

I am sure reading SMACSS has rewarded many financially (me included). It's pleasing to read your success if giving you the rewards you deserve.

If you don't get the red car you a shiny watch may do the trick, best of luck.

Jonathan Snook said on October 04, 2015

Thanks, Peter. :) Another new watch would definitely be cheaper than the car. Good plan. ;)

Alex said on October 04, 2015

You could seek a higher position with greater authority and new responsibilities/challenges, find work at a new company but maybe you just need a break from the routine, either to just get your mind off of things, to reevaluate what's important to you & identify what you'd miss if you left it behind, or to come back with an entirely new approach. Finding a new romantic interest to share your life with (assuming I didn't miss something and you're currently not in a relationship) might add a tint of pink to your current perspective and add value & new momentum as well. In any case, the fact that you have recognized that something is missing is a good start. Best of luck!

Haykel said on October 05, 2015

I think you should now give and help others. You can help with money, by teaching what you know or offering a helping hand. Easiest would be to join some association or group in your region (e.g. the red cross). I hope this helps :)

frappacanu said on October 05, 2015

I had it too.
I just had a baby and I felt that the idea of going back to work was looking less appealing. I took a year of parental leave (thank you, German government) and started to study. I switched from frontend development to UX, a subject that had always interested me and I understood, that it was the path for me. I went back to my company with some new qualifications and convince them to give me a new job in the field. they asked me to show them what I could do and employed me as a trainee for 3 months. I rocked it. now I have a new job and I couldn't be happier.

Nate Klaiber said on October 05, 2015

I decided to dive into an entirely new space and learn new subject matter. It's awesome and refreshing to start out with mostly a "blank slate" in a subject.

I still love what I do as software engineer and I use it to help me in my learning process.

jen said on October 05, 2015

Just as Kitt loves her physical activities, I hope that you find yourself back on your skates — or some other physical activity that you love. For me, getting outside or turning up my amp make life worth living.

Aside from the love you have for your boys, ask yourself what makes life worth living. If you don't know, explore interests. I believe you'll find your thing/s. Good luck!

Molly E. Holzschlag said on October 05, 2015

Noticed a cross conversation on Twitter, and realized I should read this post. Glad I did. As friends and colleagues through distance and time, I also empathize deeply in terms of plain ol' human experience. What's next? How will version .00001 of me survive and thrive. These are not little questions, nor are they easily answered. Even our parents, who typically stayed in that one-job model for their careers go through these shifts and changes, because they are less related to what we DO than who we ARE and who we are meant to be. And ya know what, we can drift into and out of these phases - it's not linear! All it means is that this time, when you feel like it, go and get that midlife sports car! Growing older does not equal giving up whimsy, fun or spontaneity! I wish you well always, Jonathan!

Jonathan Snook said on October 05, 2015

@Jen: I started going to the gym and going for walks. But it feels like a secondary goal to the thing that I want to be doing with the majority of my day/week/year/decade. That's the thing I'm hoping to discover.

@Molly: Thanks Mols. Time to order that car, then. ;)

Tony Scialdone said on October 05, 2015

A worthy next step might include looking beyond yourself and your loved ones to see how you might make a dent in the lives of others. As a Christian, much of my life is simply spent trying to serve those around me who struggle with health issues, money problems, loneliness, fear, and the like. I would (of course) recommend the same to you.

Thanks, by the way, for so much great work over the years. You've helped me a number of times, as I'm a freelance web designer. =)

Moritz Gießmann said on October 06, 2015

I had quite similar thoughts some time ago. And I'd been thinking about that "next step" a lot. The first thing I had to realize was that the progress you make slows down when you get older. Think of the progress children make compared to ours. And after all I came to the conclusion that self-fulfillment may be that next step I was searching for. Looking for what makes you happy, searching for something with a deeper meaning, maybe for a higher good beyond your own needs and struggles. I know that all that sounds very philosophical and hypothetical, but it is what I came up with after a lot of thinking. And this process is not done for me yet. I'm still in it and it takes time.

Stephen said on October 06, 2015

Jonathan, my first crisis was alarmingly similar to yours. Almost exactly. I'm still going through that, so it's good to see that there's light at the end of the tunnel (or a second "better" crisis) for someone having had similar issues. Good for you.

Floris said on October 07, 2015

Hi Jonathan, It's true, it was never about money, but about finding out what happiness really is. What you really are. If you want, check out everything you can find about Lester Levenson. He really has uncovered the secret to unconditional freedom and happiness. The keys to the ultimate freedom pdf is easy to download. Best book ever :) There are also some video's of Lester on Youtube to check out his 'vibe'. Good luck with your crisis.

Joshua said on October 07, 2015

I've been visiting since mid-2007.
I'm only 23 now, so a lot of my development in coding (especially frontend work) was influenced by your writing and examples.
I hope you find a worthy pursuit
or a solution to your troubles

As for me (nobody asked, but,) I know exactly how my life should be spent.
And I'm even arrogant enough to think that I know how most people--or many more of them than are--should be living.
Hold on, let me find a soapbox real quick...

Kitt said on October 08, 2015

I have a idea... or 20.

I do believe you know what they are, though. :)

Nonymous said on October 09, 2015

Let all your troubles to be fade away!

Scott Nellé said on October 12, 2015

Thank you for sharing your struggles and successes, Jonathan, and congrats on getting to the point where you're ready for more! I'm sure as you soul search and try things out you'll find out what your next step it. Good luck on the journey.

Andrea said on October 21, 2015

The fact that you are feeling this crisis is very important, because it means that you are ready to learn and develop new skills.
Your spiritual search is going to be far more interesting and challenging than any technical problem you have faced so far.
At least so it has been for me.
I learned a lot about myself and the pursuit of happiness studying Buddhist philosophies.
Good luck and enjoy this moment because it will bring a lot of growth!

Christopher Murphy said on December 13, 2015

I'm dreadfully late to this. Sorry, Sir. The following line resonated with me, hugely: "That which filled me with excitement has become routine." I've found myself similarly unexcited as what was once new and novel becomes everyday and, dare I say it, exhausting.

As many have noted above it might be time to embrace a new, totally unrelated challenge. Something completely different. If you have a few moments spare, I'd highly recommend Peter Drucker's writings, in particular his very short (but wonderful) book 'Managing Oneself'. It's a brief read, but it has some deep insights about addressing some of the issues you mention.

Meanwhile, sending you virtual hugs from Ireland until we meet again.

Jonathan Snook said on December 13, 2015

Thanks for the suggestion, Christopher. I've just started reading the book on your recommendation. Hope to run into you again.

Sorry, comments are closed for this post. If you have any further questions or comments, feel free to send them to me directly.