The Breakup

This one goes out to the one I love. This one goes out to the one I left behind

Relationships are both challenging and rewarding. As adults, we’ve all gone through dozens of relationships – some short, some long, some very long. They all have their ups and downs; their ebbs and flows; and their joy and pain. This is an open letter reflecting on the longest relationship I’ve ever had.

It’s been over 20 years (22, actually) since we first crossed paths. In the early days, I was so excited to be with you. I knew of you, of course, long before our paths crossed – but couldn’t believe we were together – you were completely out of my league. There was no reason someone like you and someone like me should have been together. But it worked for both of us. I think it worked better than either of us thought it would. For many reasons, you brought out the best in me. In some ways, you still do.

We both grew a lot in those early years. I gave you everything I had, and you were there to support me and grow with me. I was proud and excited to be your partner.

As with most relationships, there were challenges from time to time. I was mad at you sometimes – other times even livid. Sometimes I didn’t respect your decisions – sometimes I don’t feel like you respected mine – but as we grew older together, we both began to change and grow – but I guess that’s normal in any relationship.

The problem is that we’ve been growing in different directions for many years now. I give you full credit for the effort you’ve put into changing and growing these past few years, but for me, it’s just not fast enough. I know you want to change, but I feel like you just have too much baggage from your history to ever change enough where I can be happy with you. I want to race through life like a cheetah – and while you’re no longer the tortoise you were for much of our relationship, in your best moments, you’re still just a bear lumbering through the forest.

I need more.

What’s happening now isn’t your fault – and it’s not mine either. We grew in different directions, and now it’s just too much for us to recover. At least it’s too much for me.

I’ve been thinking of leaving for at least five years. It’s been easy to stay – you’re comfortable, and I feel safe with you.

But I’m not happy. I need more – I need to be challenged more; I need to grow more; I need to be around those who won’t be afraid to take risks and fail with me as I learn.

I took some time over the last year or so to try even harder to make-it-work. In the end, I just don’t feel like I’m getting the same from you of what I put into this relationship. I don’t feel like you truly care about me and value the things I bring to the table.

It’s just not working.

Could I have tried harder – of course. Would trying differently have made a difference – likely… but in the end, there are just too many incompatibilities for me to get over. It’s sad and scary, but I need to move on. I need to give myself a chance to have a life without you and see if I’m up for the challenge.

I’ll miss you. I appreciate everything you’ve done for me, but our time is over. It’s time for me to move on and see what I can do without you.

My last day at Microsoft – the company where I’ve spent the last 22 years, is Friday, January 20.


  1. As someone who left Microsoft weeks ago, I can very much relate with the feelings. Best of luck in your new venture!

  2. I’m days away from my 20th myself and can empathize with most of your struggle. Congratulations on making the decision to not settle for one more dissatisfying day.

  3. Can’t say I’ve ever regretted it when I left a company. (Especially since I tend to let the relationship get strained beyond repair before I go.) Good luck with finding the velocity you crave!

  4. Beautifully written… though we didn’t work together long I’m very much looking forward to your new adventures! I really appreciate someone who can be this insightful and take risks. I know you’ll rock the world and we already miss you. Light speed to your adventures on and off the mountains!

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