She said, “Halelly, if you could see me you’d see tears in my eyes right now.”
Oh no! I didn’t mean to make her cry.
No, no, she assures me, they’re tears of gratitude and awe.
“You really put it all on the line with that one question, thank you,” she whispered.
Tough decisions are… well, tough to make
Ah, life. It’s not easy.
Periodically, we find ourselves having to make really key decisions that have critical implications. And when we stare these decisions in the eye, it often feels daunting and overwhelming.
This young woman sought my counsel about a job offer. She wasn’t sure if she should take it or wait to find a better-fit option. We talked through the options.
She listed the benefits and challenges of each: Both sides have significant pros and cons!
I asked questions. I listened.
In her description of the job offer in hand was hidden her worry about missing out. If she didn’t take this opportunity that seemingly fell into her lap out of nowhere, will she regret it later? After all, there are no guarantees that if she passed on it and followed her original plan to search for a job that fully maximized her skills and strengths, she would find that ‘perfect’ job.
This job offer gave her security: a tangible, certain, and plenty challenging job offer in hand. An interesting job that she wouldn’t have really pursued otherwise, that didn’t fully match her hopes and dreams or call on her specialized skills and graduate school education. One of those serendipitous opportunities. Should she take it?
So I asked her that magic question that made her cry…
Guy and his skating dream
My younger son, Guy, is a gifted and avid skater. He’s been skateboarding since age 7 or 8 (he’s 16 now). He has long-dreamed of pursuing a professional skateboarding career.
There was only one problem he had: school.
When we admonished him to focus more on school, he’d tell us that school was getting in his way of pursuing his dream career.
Skating, like any other athletic career, is a youth-oriented pursuit with a narrow window of opportunity that closes early and permanently. You need to practice and be discovered while you’re still young. And to practice and be discovered by talent scout he needs to be out skating and not sitting in school for eight hours a day, five days a week, followed by hours of homework.
(Did that make you snicker? Yeah, sure, school – what a pain in the neck, eh? What teenager doesn’t feel like school is in their way of doing what they’d REALLY like to do?!...)
We said, "yeah, but there’s a chance you won’t make it as a skater, so you need to have a good school record so you could pursue your Plan B career."
In his infinite wisdom, Guy said: “So you want me to spend more time focusing on my Plan B than my Plan A?”
Hmmm. The kid has a point. We felt speechless - how can we argue with that logic?!
Turns out that just like child actors, singers, and pro athletes, the best way to get around this obstacle is home-schooling and/or a private tutor. That way they can get their education AND spend time pursuing their youth career track.
Guy has been nagging us to switch him out of his excellent high school to some kind of a home-based schooling solution.
But this is not an easy decision. It’s scary for us as parents: what if it doesn’t work out? What if he doesn’t thrive with a home-based schooling program? What if he struggles without teachers hovering over him to get his work done? There’s so much riding on this and it has implications for his future, not just his present.
What to do?
So we asked ourselves that magic question.
The decision-making filter question
An important lesson I’ve learned over the years is that, when you’re unsure which way to go at these critical crossroads, one of the most helpful filters through which to view the decision is the lens of regret.
It’s how I decided to start my own business in the face of intense fear and anxiety.
It’s how we decided to move from Maryland to California two years ago even though there were no guarantees it would suit us.
It’s how we finally decided to let Guy try an independent study program this semester and pulled him out of his high school.
And it’s what I asked the young woman at the job search crossroads.
Here it is:
There are no guarantees in life.
Each decision carries with it a risk that it won’t turn out as you had hoped.
There’s a risk you’ll regret making each decision and wishing you had chosen the other option.
These are all facts. No way around them.
So, knowing all this, ask yourself this question:
Which regret will you feel that you cannot live with?
Because you should strive to live a life of no regrets.
I have found that for these big, important, scary decisions, there is almost always a clarifying certainty when you use this lens about which regret is less acceptable. A clarity that helps you know how to move forward in the face of risk and uncertainty and fear.
And then you can live in pursuit of your big goals, your big dreams, and know that at least you tried. And you don’t have to live with the regret of ‘what if’ but never knowing how it might have turned out because you didn’t try.
It worked for the young woman at the job crossroads: when I asked her this question – which regret could you live with – she immediately (though tearfully) realized that if she didn’t try to find a job that matched her skills and education, if she didn’t at least TRY to go for it and make it happen but rather just settle for what’s available and easy to attain, she would miss out.
She’d regret it much more than she would regret taking a pass on the job that was offered to her now but didn’t match her initial criteria. One of these regrets she could live with. The other: it would sting much more, for much longer.
It worked when we thought about Guy’s options and their regrets. We immediately realized that we would much rather try to give Guy his dream and maximize his chances during this fleeting youthful window of opportunity than to always wonder ‘what if’.
And if the independent study fails, that’s more acceptable than to watch him grow up wondering if he might have made it as a pro skater if only we had facilitated his success. If we would just ‘play it safe’ and not take a chance, and keep him in the familiar and conservative schooling program like everyone else, we’d have to always live with that regret of not knowing what could have happened.
We wouldn’t want to live with that kind of irreversible regret.
What’s the worst case scenario if he’ll flop at the home study option? He’ll go back to the regular high school knowing we gave it a try.
We can live with that.
What about you? What’s a big decision that you’re dancing with right now, that you could try this filter on? Could you make it less agonizing in the present and live with no regrets in the future? Ask yourself the regret filter question and see what comes up for you.
I’d love to hear about it – you can put it in the comments below or send me a private email, whatever you prefer.
And send this post to someone you know who might be struggling with a tough dilemma at this moment – it could really help them break through the impasse!
Whatever you do, I wish for you that you live a life of no regrets. You’re worth it!
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