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Author: Steve Ainslie

Kinda Ugly

Posted on July 25, 2022January 29, 2024 by Steve Ainslie

The #1 suggestion for being more successful using dating apps is to use good pictures. Any dating app site, any dating advice podcast and any person familiar with online dating will parrot this. I fell for this trope when I was using Bumble and Hinge. First I used the pics I had on my phone….

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Pretending Not To Care

Posted on July 25, 2022 by Steve Ainslie

My mother often says, “It’s no big deal” to dismiss whatever feelings she has about a situation and end a conversation about something that might trigger an emotional response. No wonder I did the same thing for so many years of my life! I used to stuff down my fear, excitement, wonder and joy to…

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Retirement Fantasy Vs Reality

Posted on July 24, 2022 by Steve Ainslie

When I was in my 30s, I would fantasize about someday being able to retire. At the time, I was working for tech startups. I enjoyed the work, my colleagues and the challenges. I liked that my income was going up rapidly. I liked having a reputation as a “go to” guy who made things…

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No More Craigslist

Posted on July 23, 2022 by Steve Ainslie

When I first became aware of Craigslist in my city, I thought it was fantastic for buying and selling used goods. Before Craiglist, selling something meant placing an ad in the local paper and paying $20 for 4 lines of text running only 2-7 days. Then you had to hope a potential buyer saw the…

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Chop Wood, Carry Water

Posted on July 22, 2022July 22, 2022 by Steve Ainslie

A Zen Koan says, “Before enlightenment chop wood, carry water…After enlightenment chop wood, carry water.” I first read this when I was learning yoga from Doug Swenson’s Ashtanga book in 2009. It has stuck with me ever since. Another phrase that has stuck with me for years is, “If your job is to sweep floors,…

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Money Unmotivated

Posted on July 21, 2022 by Steve Ainslie

It is so strange to care so little about money anymore after sending most of my life yearning and striving to become wealthy. I’m never got there. I am early retired. I live off of investments and savings until social security kicks in. My life is relatively comfortable, but it involves compromises I wouldn’t make…

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Cereal Killers

Posted on July 21, 2022 by Steve Ainslie

When I was about 4 years old, we moved into our first home and I had my own bedroom. My parents bought me a nightlight so that I wouldn’t be scared of the dark. It was so bright that there was no way I could fall asleep with the nightlight on. So instead, I lay…

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Aging Well

Posted on July 20, 2022April 19, 2024 by Steve Ainslie

My Aunt Essie used to jokingly call herself an “Old Maid”. She was a retired elementary school teacher who never married. Essie lived in the home that her parents raised her and her 12 siblings in. She shared the downstairs apartment with her brother -my Uncle Bob. Upstairs in a separate apartment, lived her other…

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The Winemaker

Posted on July 20, 2022 by Steve Ainslie

During the dotcom boom in the late 1990s, there was a high flying tech startup named FreeMarkets. They made quite a splash in my hometown of Pittsburgh. I remember meeting the two founders during a happy hour on a rooftop bar when they had a few dozen employees. Two years later the company occupied a…

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Kids, Purpose and Missions

Posted on July 18, 2022 by Steve Ainslie

A friend whom I hadn’t spoken with in years reached out to me last week. In the course of catching up, we talked about work, family, children, retirement, mission and purpose. He talked about wanting to “give back” to society in a meaningful way. He’s considering fostering under privileged children or mentoring them through big…

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