My one rule for making big decisions
I gave a talk to The Grommet team and to the teams at Mass Challenge on this topic. It’s had more impact than I expected, including this great Medium post by Julia Barry .
Here is the post, reproduced in its entirety.
For Jules Pieri, the process of making a tough decision requires one essential step: the firm and deliberate conviction to abandon all regrets about the potential consequences of that decision.
MassChallenge recently gave a warm welcome to this year’s 128 finalists as they settled in to their new office space at 21 Drydock Avenue. To kick off the 4-month accelerator program, the startups participated in several structured days of “Boot Camp,” a series of intensive training sessions and talks intended to help the startups maximize the opportunities they will have throughout the coming months. As part of Boot Camp 2015, Jules Pieri gave a captivating and informative speech explaining her unique “no regrets” approach to decision-making.
Jules Pieri is the founder and CEO of The Grommet, and thus had some valuable insight to share based on her personal experience as an entrepreneur.
She began by asserting that big decisions generally correlate with big life goals. According to Jules, our major choices in life should, and usually do, align with our long-term ambitions. For her, those goals were getting out of Detroit*, making a substantial, positive impact on the world, and simply being a good person. All the big decisions she has made in her life have been in keeping with those three objectives.
Ever since Jules was a kid, the words “I wish” made her skin crawl. She emphasizes self-empowerment and action rather than theoretical, wishful thinking.
Along those same lines, she has adopted the expression “no regrets” as a sort of mantra for making big life choices. One way Jules can tell she’s crossed into her “no regrets zone” is if she has never before done what she’s about to do, and probably doesn’t know anyone who has.
This never-look-back approach to life may appear a bit idealistic and far easier said than done, but Jules Pieri heeds her own advice. Right around the time she was offered a very lucrative position at eBay, Jules realized that her father didn’t have much time left. She had wanted very badly to throw a party for him, and she knew she would not be able to put in the thought and effort necessary to make it special if she took the job. “If I had gone with eBay,” she said, “I would have owned a small island by now… but I turned it down.” Though some might widen their eyes and shake their heads at such a so-called “missed opportunity,” Jules maintains to this day that she does not feel an ounce of regret for this decision. She threw her dad an unforgettable party, and she would not trade any amount of money for the happiness he felt.
Jules also presented some advice to early-stage startups. “Other people are essential,” she said — a support system of some kind (be it friends, family, or professional networking) is absolutely crucial. She offered comfort to the startups by sharing that anxiety and ambiguity are to be expected in the beginning stages, and that they are normal, integral components of entrepreneurship.
Of course, Jules acknowledged, there are massive amounts of fear that come with the process of founding a company. To talk herself through that fear, Jules has a calm and practical outlook: during The Grommet’s fragile periods, her brother would often ask, “What if it fails?” and she would respond, matter-of-factly, “I’ll get a job.”
–End of Medium Post–
For anyone reading this: I recommend that you take ten minutes to record the top three goals of your life and look at them every five years or so. It does not count to say generic things like “Be happy, Be healthy” or “Raise my children well.” Who does not want to be healthy, happy or be a great parent?” Including those could be a waste of a goal. But if you want a family and have not yet found a partner, that could be a top life goal.
My three goals (in bold type in the Medium post, above) have remained unchanged since I was 25, but in surveying of my contemporaries, that is pretty unusual. I do think I should replace the “Get out of Detroit” one because if I never got to take another big trip in my life, I would already feel that this goal was achieved.”
You might wonder if my own intent to “Be a good person” is also a really generic goal. Let me explain: I don’t mean this “good person” as following Ten Commandments stuff–which would be very generic. I keep it as a top focus because for me that has a lot to do with “showing up.” I.e. going to other people’s important events. And in almost every case those events are inconvenient and sometimes costly, but I often jump through hoops to be present. If I did not consider this a very top goal I would probably flake out more often–and at the end of my life I would deeply regret that.
*This is over simplified–I really wanted to see the world and live in different places. But I guess at a basic level, that did mean getting out of Detroit.
Jules Pieri 
One Response to “My one rule for making big decisions”
[…] Being able to do this has no age limit. Middle aged people can be paralyzed by fear of discomfort just as easily as young people facing hard things for the first time. But the young person who starts developing the navigational skills and self-awareness for mastering fear and discomfort will build the life they really want, with no regrets to hold them back. […]