18 Comments

I love the positivity of this article. Never too late for anything. Never too late to stop, never too late to continue! Great photos too!

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Your story is enriched by the photos. I'm a bit older than you - I just turned 71 on the day of this post, October 11 - and I'm still aspiring to have the garage you left behind! The math hasn't worked for us, but it's getting better. Out of necessity I freelance long hours, but it is something I love. A few steady clients, they need me and I need them. Mutual interdependence has a way of keeping me young. I'm glad we met on Substack! This is a great platform for the old and the restless. Cue the sappy soap opera music.

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right! For sure we not have met without the internets. I’m a little envious of you Frank, I’m trying to build a set of clients right now that I can keep working with over the next 10 years because I’ve learned we all need that connection and sense of accomplishment. And doing something that’s creative!

Happy Birthday Frank, wishing you many more

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Don't be TOO envious! You are seeing and doing things that I only appreciate online, vicariously.

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Also 60, leaving tech after 25 years in docs teams, everything's paid off, this was the goal, and now I can try to revive the dead literary career I had to abandon because writing books pays nothing, and I had people to take care of. A little nervous! But stoked ... I've got 3 books sitting around this house like cars on blocks. Time to put all the pieces back on and see if I can get them to start up.

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Nice Charlotte! I feel the same although I never had a literary career or the time for such aspirations before. I'm making my way through similar stacks of books and trying to improve my writing a little bit better every post. I like your visual of taking them off the blocks

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Welcome to the freelance world, Andrew! My last job was with a company acquired by MS, and I've been freelancing websites from home since then... 2005. I love hearing good stories like this. Have fun with your new gig!

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Thanks for the welcome Tony! It's nice to know this territory is not uncharted

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Excellent hearing about your past. Hope to hear more about working at Microsoft, if there are some fun stories about how you and Steve Ballmer hung around together...I know you will do well in this chapter of your journey!

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tx Paul! it feels like this part of the map has the least directions but I'm fumbling through it. My MSFT career arc spanned 3 CEOS and I had run-ins with Bill, Steve and Satya. Maybe that would make a good article ...

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Sure would be interesting. A 3 article series. What I taught Bill Gates, Steve Ballmer, and Satya Nadella. 👀

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lol could fit that on a post it 🤣

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that would be awesome, Andrew!

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Congrats on making the leap! I’ve got another decade or two of kids with a lot of expenses, but I do hope to make the leap to working for myself at some point. (5+ years from now. Daycare is expensive!)

That will probably result in me working more, not less, but will hopefully be more rewarding.

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Tx yeah the kid timing thing cannot be overlooked; for us JFran took some time because $ but also to hang out with them. I've always wanted to run my own thing and while I can half ass it a bit I find it really rewarding

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Being able to work at 150% when you want and half ass it when you want is the dream!

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Hey, this is a really joyous take on this story! Really fun to read it.

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tx Tom! I really appreciate that coming from you

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