The New Rules of What-If

Years ago, I had a similar experience, though on a much smaller scale. The firm I worked for, Otec Inc., offered me an opportunity to partner in developing a new online jobs board. Although the idea of creating a startup enterprise was enticing, my position as an executive recruiter was morally fulfilling. Plus, the client relationships and goodwill that I had built over time was not something I was willing to walk away from. So after some serious consideration, I eventually declined the offer. The new startup venture went on to become and was eventually sold to Yahoo for millions. Some of my co-workers who took the leap of faith essentially retired after that and continue to reap the financial rewards.

When I look back on this choice however, I rarely feel regret. I know that I made the best decision that I could, given the self-awareness and information that I had at the time. Like they say about dogs (there are no bad dogs, just bad owners) – I would say the same is true of our decisions. There are no inherently “bad” decisions, just poor ownership of those decisions. Most of us make decisions with insufficient data. When it comes to making choices, we all do the best we can with the knowledge that we have, and then we must let go of the outcome. Letting go means no regrets, no second-guessing, no self-recrimination. Letting go means being easy on yourself no matter what happens.

One of my clients was recently struggling with a thorny dilemma. She was trying to decide between staying in her current job which offered an enticing promotion, or going back to school for an MBA. “Taking the position feels a bit like jumping into shark-infested waters,” she said. “But I fear that coming out of the MBA program, I may never be offered another opportunity like this again. I also know I want to have kids, and getting out school at 37 with no job and no money is very scary! I once dreamed of having this job title and now that it’s in front of me, I’m not sure I even want it anymore.” Sound familiar?

In her book The Joy Diet, Martha Beck outlines questions to ask when considering any course of action:

1. Does the thought of taking this step create an inner sense of clarity, despite my apprehensions? (When a risk is good for you, you may feel apprehension, but little or no confusion.)

2. Do I feel only fear, or is there also a sense of toxicity akin to disgust? (Pay attention here: a “good risk” feels like taking a high dive into a sparkling clean pool. A bad risk feels like taking the same leap, but into polluted swamp water)

3. At the end of my life, which will I regret more: taking this risk and failing, or refusing to take it, and never knowing whether I would have succeeded or failed?

I find these questions are useful in discerning fear from excitement, which often can look very alike.

But what if you’ve already made your decision and it turned out to be the wrong one? That pernicious little voice pops up in your head and begins to chatter loudly: “You saw the red flags and still you ignored it! Boy, you really screwed that one up, didn’t you?” To regret past decisions is to reject yourself, and worse, it means overlooking the lessons they have bestowed upon you. It is also a powerless victim state that prevents us from moving forward. Look, we all play the What-if game on occasion; we wouldn’t be human otherwise. But the trick is to play the game only going forward, not backwards.

If you must play the What-if game, here are the new rules:

Ask only What-if questions about the future:

What if I were to embrace this new opportunity whole-heartedly, what are the potential rewards it may bring? What if I were to take that trip that I’ve always wanted to do and make it a priority for this year? What if I were to offer my candidacy for that job that I just know I can do better than anyone else in my firm?

Stop beating up the younger version of yourself:

The concerns you had at 25 are very different from those you may have at 35, 45, or 65. We are constantly evolving in body, mind and spirit. So we can rightfully expect that our priorities will change over time too. Don’t judge yourself unfairly or keep punishing yourself for some perceived error in judgment. Remember, you were a different person then and you did the best you could. Let it go!

Learn to recognize assumptions:

Human beings, it turns out, are very bad at predicting the future. We’re even worse at predicting what will bring us happiness. So don’t assume that you know where a particular path will lead you. Rather, ask yourself “Does this look interesting? Could this be fulfilling or enriching?”

Ultimately, the choice to let go of all our previous decisions (good, bad or indifferent) is a heroic act of forgiveness. But trust me on this; it is the best decision you will ever make. When you are able to give thanks for everything that has happened in your life, then you are truly free.


Ann Mehl is a certified Martha Beck coach specializing in life and career transitions. A former executive recruiter, she assists individuals who feel stuck in their lives or simply need a plan to jumpstart their careers. Through one-on-one counseling, Ann guides clients to listen to their authentic selves and focus on their personal growth. As a runner who has completed over forty marathons worldwide, she lives what she preaches. Ann has helped numerous men and women in reaching their personal...

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