The “when” to “if” problem

I would venture that one of the more painful personal and emotional transitions we go through as humans is the when {something will happen} to if {something will happen} transition. There are literally hundreds of examples of this possibility, including:

• Kids
• Marriage, relationships
• Promotions, work advancement
• The Rona virus

When you have to change your thinking on a topic from “when” to “if,” it can pretty powerfully adjust who you are. Let’s do an example through the kids prism.

“When we have kids…”

I got married (I am no longer married) in March 2013. I grew up in what some would describe as “upper middle class” in New York City. I didn’t have any cliched Southern approach to family-building, and my parents had me (I am an only child) late — my dad was 40. That said, I think I had the general notion, from observing my friends and just middle-class market existence, that I would get married and then, poof, eventually there would be kids within 1-2 years or something. That’s like, how it works, right?

Well, obviously for millions of people that’s not how it works, but my ex and I never really “tried.” We had discussed it a bunch, and we “tried” for maybe one month in early 2015, and that was it. We were divorced in early 2017. Now, maybe and hopefully I get another chance at all this. For now, though, I need you to go back to May 2013.

I was living in Minneapolis at the time. We had been legally, and church, married for about two months. It was Mother’s Day and we were eating somewhere in Uptown Minneapolis. I remember I said something to be cute, like “Well, maybe this is your last Mother’s Day not being a mom…”

When we have kids…

By 2016, in Texas now, having tried for barely any time at all, now the discussion was this:

If we have kids…

Now look, I don’t fault my ex for any of this. I was broadly a drunk at the time, and I could see her not wanting to bring kids into that. It was the subject of a few arguments along that arc.

But when became if, and now something you just expected from your life is perhaps a distant non-possibility, and it changes you.

The Rona virus

You know this drill — >

When things return to normal … was the rallying cry.

That became:

• If things return to normal
• “The New Normal”
• “The Never Normal”

See the power of the transition? The “when” portion is a presupposition of business as usual, friends as usual, society as usual, bars/restaurants as usual, “all will be OK.”

In the moment you shift to “if,” now fundamental things you believed — assumed, yes, but all assumptions are beliefs at some level (what else is God, honestly?) — have changed.

There is a new state.

“When I meet the right person…”

… this is another big one. It happens to millions of people every day. It’s just a question of how comfortable they are discussing it with those around them.

“When I meet the right person…” can fade to “If I meet the right person…” and whole structures and ideas about your life are different. Are you doing an Elizabeth Gilbert and traveling the world solo? Are you getting pets? Are you doubling down on apps?

Decisions result from the language shift.

So is there a path through all this?

Somewhat. From here:

A lot of life is, frankly, a cluster fuck. No one really knows what in the shit they’re doing most of the time. We all try to follow some model or “be a good person,” but a lot of us have no clue.

Because there’s a high level of uncomfortable-ness in society but we kinda push it down and try to lead our curated best selves bullshit, I think that when you find someone who can really take a bath in being uncomfortable, you’re like “Whoa, I remember that person!”

I actually often try to live my life this way. I wouldn’t necessarily call myself successful. But I’m out here doing something, I ‘spose.

Lean into the skid. Talk about the uncomfortable shit. Throw out the dumb shit into the world. Be memorable.

Seems like as good a plan as any, right?

The bottom line, sadly, is no matter how passionately you feel about something (having kids, getting married, beating The Rona, getting promoted, owning a nice house, whatever whatever): You are ultimately promised nothing and have to do the best with what arises through a mixture of timing, luck, your talents, your shortcomings, and just general life.

You need to play with the hands you are dealt, and if getting one specific hand is more important to you, try to position yourself as best you can to get dealt that hand. That’s part of why people get married at 22, yes. Sorry to be too honest here.

Quick personal plug: May 8th panel

A lot of the above was about personal stuff, but can easily be applied to career and business-building blocks of your life. All this said, I’m part of a panel on May 8th (digitally) about leadership in crisis, dealing with change, new realities, transformations, etc. You can learn more about the panel, and even register for it, right here.

When you register for the panel, you’ll get some cool ideas on life and work — but if you choose not to, it’s OK and I’ll deal. No worries. But I’d love to have you too.