Winding down a career

Let me get some clarity first before I start.


– a profession for which one trains and which is undertaken as a permanent calling (Merriam-Webster)

– an occupation or profession, especially one requiring special training, followed as one’s lifework (

– a career is the job or profession that someone does for a long period of their life (Collins Dictionary)

Winding down

– currently on a 3 to 4 year plan

When I look at those definitions for career, two out of three ain’t bad comes to mind. Thank you Meatloaf! Permanent calling wasn’t exactly permanent and I guess I should frame this up a bit before we move on. Winding down may very well mean another 3 to 4 years. Before winding down though I’ll discuss ramping up.

In 1984 at 18, I entered the army as a professional punk fine tuned in doing the least amount of work as possible and extremely skilled in partying and chasing girls. What better job to select then a military policeman. Go figure. After 4 months, I knew I had made a tremendous mistake but Germany was wunderbar and the army babysat me – fed, clothed, and housed me through those wild years of 18 to 21 for a young man.

When discharged I got on with a job with the Postal Service sorting mail in a facility. I had the title of mail processor. My dad told me I had it made. Good money, great benefits, and guaranteed stability. I lasted there 3 years where I couldn’t take it anymore doing the same task everyday. My little brain said we can’t do this anymore. As someone who hated school I understood if I was to find any sanity I needed to get an education.

I successfully screwed around enough at college picking different majors and on the 5 year plan. My debt was getting high so like many other stumblers I ended up getting a major in Communications and a minor in Information Services(computer programming). The minor was my real interest, so after graduating I had to leave beautiful Colorado to get some experience in that field in Illinois. That was a hard pill to swallow and a growing up moment.

So that takes me to becoming an application developer building web applications and now working on mobile applications. In 1998, I got back to Colorado and started the job I’m at now. I got my masters in computer science and started climbing that ladder to becoming a senior developer. In the beginning it was great. I was fired up and loved working closely working with departments within the hospital and building them apps that would make their jobs more efficient. The salary grew and grew and often like many folks I kept biggering and biggering with bigger houses, bigger vehicles, and investing in real estate. The cuffs were a shiny gold, but I was so busy I didn’t notice them right away. Somehow the bills got paid with the minimum payments and we squeaked by each month.

After 10 years, there were thoughts of what would it look like to head a new direction and try something else, but at that point at least in my mind and on paper that wasn’t a possibility. More years went by, the divorce, and 6 more years of digging myself out of that mess – you find me here. Twenty-three years with the same company and approximately a total of 27 years in the same “career”. I’m burned out on tech. The passion has become a ghost long gone and I’m so over sitting behind a computer.

Winding down

So here we finally get to the juice of this post. Like many of you, I’ve discovered blogging is often more for me to work through my shit.

So why not just quit now and do something else? The thing is right now there isn’t something else that’s burning from within that I want to go chase. The other main theme is that now is the period winding down where I can start setting myself up for future success. I’m making the best money I’ve ever made and yes I can hear many of you balking at this with the thought money isn’t everything. I agree. But at 56 I’ve done a lot of living and learned much through going into debt, living that life, and eventually and I mean eventually after many many years coming out the other side. Debt was a living hell just as much as abusing alcohol for forty years. I’ve worked too hard to get myself debt free. Just like getting alcohol free. I’m not going back there.

I have freedom now to choose my next paths. I have freedom to focus on funding my retirement accounts and to start exploring and planning my encore years. At 56, I’ve set myself up by hard work, sacrifice, and learning from my past and using that wisdom to make good decisions. So when my boss asked how much longer I thought I’d work for the company, I told him I’m hoping I can make it till I’m 60.

So what will I do as I wind down from this career? Explore. As many of you know I started a walking and a rucking group. What does that have to do with deciding on what I want to do next? Absolutely nothing, but it is an interest and I get so much joy from it and right now that’s a sign to keep following it. I discovered I get so much out of connecting with others face to face. I also just started tutoring a young child through the Childrens Literacy Center. Who knows … I’m staying open and putting myself out there.

It sounds like you’ll be searching for another career? Doubtful and this just became clearer. I think there will be many little gigs I end up exploring. 60 is still young and I have a lot of energy and love to give. I know I’ll take some time to travel, so right now I’m planing becoming a nomad for a few months out of the year living in a van traveling through the States and Canada. Living in a studio in Germany for a month to immerse myself in the culture is also on my list. Maybe even bike across the US and do the Camino de Santiago! So many great opportunities and winding down instead of jumping ship helps make this all possible.

Careers may be a great option for those starting out, getting married, and having kids. When I’m 60 though I’m thinking fuck that noise. Ha. Envision a big movie screen with a firm middle finger coming into focus! Well I rambled enough for now, but it has helped me to start make sense of this new stage of my life. If you’re still here reading this – I thank you!

Dwight 🦋

Meat Loaf! Love this❤️

15 responses to “Winding down a career”

  1. I totally get this, Dwight. I’m hoping to retire in a few years myself, and I’m really hoping I’ll be well enough to do a lot of similar things as you have on your list. I’ve been eyeing a lot of vans and tiny campers, making plans… I’m excited for you!! 😊

    Liked by 2 people

  2. 13 years till retirement for me and i best start thinking on this. I have been a nurse now for over 20 years . If i stay in my current field ( private duty) i can probably make it to or past retirement. So thats probably what i’ll do given that i just bought a house a bit over 2 years ago. I did refinance and will likely do it again.With all the unexpected medical bills i am not sure where i will be in 13 years though and it is a huge concern. I am healthy over all, but even so- it all adds up.I guess i am kind of swimming atm. I would like to check a few things off the bucket list though- like competing in bodybuilding in the over 40 class.

    Liked by 2 people

    1. Oh yeah! Get on that competition goal. that would be so cool!

      Liked by 2 people

  3. Your plans for your encore years sound fabulous. You’ve come so far… continue setting yourself up for the adventure! 💛🌟

    Liked by 1 person

  4. I’m growing accustomed to the space of ‘winding down’, and believe we deserve it. Being in the customer happiness field, I’ve not thought about retiring because it’s connected to my permanent calling. Recently, I’ve been pondering traveling, even if it’s just for a weekend to a nearby town, but the Camino de Santiago has always been on my heart to do. Keep following that heart spark Dwight.

    Liked by 1 person

  5. I retired from teaching at age 60. But I am glad you are figuring out ideas now. I didn’t do that at first, which made it a bit harder.
    The freedom is wonderful!

    Liked by 2 people

  6. Lots to consider and wonderful to have options!

    Liked by 1 person

  7. My husband agrees with you on the wind down strategy. He picks up a bit of work if it interests him, and he goes and does one of his other projects if no work is bubbling. Then he’s content either way. Actually, sometimes he gets crabby when someone needs him to do some work. He’s got so many other hobbies, plus fellow winder-downer friends to hang out with that work cramps his lifestyle ha ha!

    Liked by 1 person

  8. The freedom of choosing your path is a wonderful gift and I agree careers are for the young – you will bring wisdom and your big heart to whatever you do Dwight 💕💕

    Liked by 1 person

  9. Thoroughly love your future options/plans! They will definitely keep you trudging along at your current job. 👍🏻😃

    Liked by 1 person

  10. Way to go Dwight! I hope it all works out for you. 💞

    Liked by 1 person

  11. There is so much more to life than being gainfully employed. I’m sure you won’t be bored, whatever paths you will be traveling on in the future.

    Liked by 1 person

  12. I love this Dwight! Good for you! You plans sound amazing – freedom to shine, to explore, to be, to do whatever moves you! I can’t wait to hear how it all unfolds! 🙂
    P.S. I love Meatloaf too! Sorry to hear of his passing.

    Liked by 1 person

    1. FINALLY, someone who likes Meatloaf!!! I knew you were cool : )


      1. Dwight, who couldn’t like Meatloaf??? One of my top fav albums (yup showing my age with the word album) is Bat Out of Hell….LOL

        Liked by 1 person

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