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Rest, Reflection, and Recharge – An Entrepreneur’s Thanksgiving

It’s Thanksgiving in America, the time-honored tradition where we all take the opportunity to pause, reflect, and express thanks for the many wonderful things in our lives.

The beauty of Thanksgiving is found in its simplicity. There is no expectation of gift-giving, no commercial campaign with retailers spending millions to gain access to your wallet, and no mythical creature visiting your home for the holiday. The entire holiday boils down to enjoying a single meal with family and friends. What’s not to love?

Without a doubt, Thanksgiving is my favorite holiday. Each year, I look forward to the opportunity to slow down, catch up on rest, and connect with some of the most important people in my life. As part of the holiday, I’ve created a couple rituals that give me the chance to slow down and reflect. I don’t slow down and reflect nearly enough, so having a holiday with a few extra hours is a rare opportunity that is simply too good to pass up.

First, I actively participate in a family tradition where we stand around the beautiful Thanksgiving dinner table prior to starting our annual feast. As we stand together as a united front, we start to go around the table with each of us, one by one, sharing what we are thankful for. We listen to each other with high levels of empathy and respect, but without distraction or judgment. After completing this tradition every year, I find myself feeling more connected with the family and friends sitting around the table with me.

The shared experience of listening to others and speaking about what each of us is thankful for goes a long way towards creating real meaningful relationships amongst my family and friends. I’ve found that this same principle of group reflection can also pay amazing dividends in a professional setting (because we all know “professional” is how to describe life inside a start-up).

At a recent company anniversary at Grand Circus, the Google for Entrepreneurs tech hub in Detroit I co-founded, we went around the room to share our favorite company moment to date. It was a lot of fun hearing about what burned the strongest memory in everyone’s mind and it helped all of us appreciate the fact that together we created something great. There’s no doubt discussing shared experiences and sentiments brings the company values to life in a way that reciting a mission or posting words on a wall will never be able to.

Secondly, at some point during the holiday I separate myself from the wonderful hullabaloo and commotion of Thanksgiving for an hour, where I do nothing but sit and write. I prefer pen and paper because it forces my thoughts to slow down and proceed at the pace of my handwriting. I start with what I’m thankful for and allow my thoughts to take my writing in whatever direction they so choose. I’m hard-wired to always charge full-steam ahead, but allowing myself to take the time to write gives me a new sense of clarity and meaningful areas of focus. I always find myself extra-charged coming out of Thanksgiving and into December. It’s Thanksgiving, so we all have the time to pause and write. Why not give it a shot?

As an entrepreneur, we all have so many things to be thankful for. Here are a few things at the top of my list as I continue to swing for the fences:

A Perfect Litmus Test.

No matter what month of the year it may be, when challenging moments arise I envision myself sitting in Springfield, Illinois on Thanksgiving Day. I know on Thanksgiving that I’ll be sharing the highlights and low-lights from my personal and professional endeavors with my family. You see, in my family you’re sure to have people ask you a lot of questions and the family always finds a way to tease out the most important things happening in your life.

I like to apply something called, “The Springfield Test” to situations I face throughout the year. Here’s what I mean…during the entire year, as challenges arise, I ask myself if the outcome from the situation I’m facing will actually be meaningful when Thanksgiving in Springfield rolls around. I know I’ll answer a lot of questions from family, so if I realize the results of my current situation won’t be important enough to come up during the Thanksgiving day questions, the topic has officially failed the Springfield test. At this point, I recognize the situation is not worthy of my time or emotional energy. If, however, the answer is yes….you can be sure I’m going to spend a lot of time, energy, and effort to get the best outcome.

Do you have a Springfield test?

The Village that Surrounds Me.

Entrepreneurs simply can’t be successful on their own. It’s not possible to create a great company going solo and even if it were possible, it would be a terrible idea. At every turn in my career, I’ve had amazing friends, mentors, and family members supporting me. I’m thankful for the people in my life who have given me an unbiased view of the situation I’m faced with and shared words of encouragement. I’m thankful for mentors who asked tough questions of me, and especially those who consistently did so on nights, weekends, and during their busiest days of the year. To me, a true friend is someone who you can count on to give an honest opinion…not someone who tells you what’s comfortable to hear.

Too Positive to Be Negative.

There are a handful of people in my life who always put me in a better mode after interacting with them. These people provide amazing energy that I feed off of. They smile, they talk with passion, and they find the silver lining in everything. I love being surrounded by people who see the good first and are simply too positive to be negative.

Colin Powell was dead on when he said, “Perpetual Optimism is a force multiplier.” I’m grateful for all the smiles and positive energy the people in my life bring me on a daily basis. I’ve found that I’m only successful only when I believed 100% in what I was doing. The positive people in my life are the ones who have truly allowed me to believe in what I was doing day in and day out.

The Journey.

I love the challenge of trying to figure things out every single day. There’s no end game as an entrepreneur. After climbing what once seemed like an insurmountable mountain, we always find another peak to climb. Often, we had no idea that this peak even existed before we climbed the original mountain….but that’s what keeps the first burning hot in our belly.

You can’t get a second customer until you have the first and you won’t get that million dollar deal until you’ve scored a $100,000 deal nine times out of ten. I’m thankful for the ongoing challenges I get the chance to overcome. I’m energized to solve those challenges and climb the ever-receding summit.


It’s Thanksgiving and I hope you’re able to appreciate the many great things happening around you. Go ahead: pause, reflect, and get clarity in your journey.

Press on my friends.

Press On.


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