Asleep At The Wheel

It’s a well-documented fact (on my blog at least) that I was asleep at the wheel for many years of my life.

From age 15 to 35, I made most decisions under the premise that if other people approved of me, then I could approve of myself. Even putting in 70 hours a week at the office didn’t seem good enough, didn’t seem dedicated enough, didn’t seem impressive enough.

Because I collected a lot of titles and trophies throughout my career, most people assumed I was addicted to success. But I knew I wasn’t addicted to success…I was addicted to approval.

Thankfully, those days are behind me.

I learned from them, I grew from them, and I’ve been able to move past them. Thanks to my favorite self-help books, a life coach, hundreds of Oprah episodes, and more than my fair share of red wine, I finally woke up.

I developed deep love, appreciation, and respect for myself and as a result, I made a pact never to live my life in hopes of impressing other people again.

My life now is very different — it’s very peaceful, very calming, and very normal.

However, I’m not blind to the fact that there was some collateral damage that came along with the way I used to live my life.

I was a lousy friend and family member. When you spend most of your time trying to impress other people, it leaves very little time and energy left over to be a good person. I was the friend who showed up late and empty-handed to every party. I was the daughter whose meal contribution to the ski vacation was frozen pizza. And I’m horrified to admit that once I was two blocks away from showing up to a “stock the bar” party after the loss of a friend without anything to stock the bar with. My goodness.

I was really unhealthy. When you spend too much time at work and you love chicken tenders and french fries…you keep eating chicken tenders and french fries every day, regardless of what it does to your health. A few years ago, people thought it was so “cute” that a 35-year-old ordered off the kids’ menu, but the truth was that I didn’t care enough about myself to take care of myself.

Thankfully, those days are gone.

Now, I know how to make a mean appetizer for any occasion. I’ve got a bottle of wine stashed for a neighborhood party at a moment’s notice, my french fries have been bumped for Brussels sprouts, I’m borderline obsessed with yoga and meditation, and I just got an incredibly clean bill of health from my doctor.

In addition to the collateral damage to my personal health and happiness, this time of year takes me back to my inadequate knowledge regarding local politics.

I’m embarrassed to admit that four years ago, as I was driving to the polls to vote for the next President, I called my older brother in a panic. “Hey! I have no clue who to vote for at the bottom of the ballot. Tell me which boxes to check.” My more informed big brother gave me his opinion, and I immediately began reciting the candidates’ names in my head because I’d never so much as heard their names before. Then, I walked into the voting booth, without a clue what I was doing and voted.


I suppose it was a step forward considering that I had never voted for any office other than President my entire life. Just to put that last statement into perspective — I was born and raised in Richmond, Virginia. I’ll live the rest of my life in Richmond, Virginia. And I even imported my husband from Geneva, Switzerland to live in Richmond, Virginia. Yet, for my entire adult life I never even voted for mayor of the city that I love so much.

Not anymore. This year I’ve done my homework.

I’ve read what the locals and the Economist had to say about the race, I’ve attended meet and greets, I’ve watched the debates and finally, for the first time in my life, I have an opinion.

Jack Berry is the guy for the job. Jack Berry should be the next mayor of Richmond.

jack-and-katRichmond is on fire when it comes to being recognized for amazing restaurants, outdoor life, entrepreneurship and even hosting global sporting events. The next frontier will be to have city officials committed to progress and reform for those families committed to living and thriving in this great city.

Jack is by far the most experienced candidate on the ballot – with significant city and county government experience followed by a decade as the CEO of Venture Richmond. He’s also, in my opinion, the most empathetic candidate in the race. He’s committed to helping the amazing individuals and communities in Richmond who have been left behind.

The Richmond Times-Dispatch just endorsed  Jack Berry, and I couldn’t agree more when they said that Jack is a skillful and determined builder of bridges and relationships and that he’s in it for the right reasons — to make Richmond a better place to live, work and learn.

I just endorsed Jack, myself, in a video as well as in his latest television commercial.

govoteFour years ago I was asleep at the wheel, but I’m not anymore. Not when it comes to my life and not when it comes to my city.

I’ve turned a lot of corners since I last drove to the polls and called my brother on the way. Four years ago, I was oblivious regarding what it was like to be a good friend, a healthy human being and an engaged citizen of Richmond, Virginia.

My, what a difference four years makes.

I’m proud of how far I’ve come — from forgotten friends and eating french fries to cooking tofu and starring in political television commercials.

When you know better, you do better.

It feels so good to be doing better.


Join the discussion and tell us your opinion.

Tasha Turpinreply

Hi Katherine!

This post touches on what you talked about at the Women in Private Investing Lunch back in September. I felt like you have experienced exactly what I am currently experiencing. I want to be certain that my success is based on what I consider success and not what everyone else considers it to be. When you mention the trophies and the titles, I thought, that is what defines success. But does it really? I’d love to talk more about your experiences.

Katherine Wintschreply
– In reply to: Tasha Turpin

Thank you, Tasha. Often people confuse success with happiness and I was one of those people for the majority of my career. It feels great to be on the other side of it and I am proud to say I’m happier than ever. I recommend reading Finding Your Own North Star by Martha Beck. It is one of my favorite self-help books.

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