The HOW Conundrum

No. 106: When it's useful, when it's restrictive, when it's a crutch

My dear reader friend,

I recently participated in

Dawna Kreis

’ Infinite Possibilities workshop and found myself challenged in one area. (OK, maybe more than one area, but this will get too long!) I appear to have the “curse of the HOWs” — a need to know the plan before committing to a goal.

Photo by Zachary Kadolph on Unsplash

In fairness…

I spent two decades as a consultant. Clients hired us for our HOW knowledge: to teach them how to do things or to do it for them. Like many professionals in the field, my career was built on being an expert who knows HOW.

So, one could say figuring the HOW is my default position. Now, here’s Dawna telling me I shouldn’t worry about it — that knowing the HOW isn’t important. Wait... What?!?

Dawna’s a nice person, and since we’ve just become friends, I didn’t want to overwhelm her with all my neuroses at once — these things need to be revealed slowly, or you risk scaring people away! So, I nodded and took notes, even though I was internally conflicted.

But the question about my apparent HOW dependence stayed with me long after the Zoom sessions. I’ve been thinking about it and catching myself whenever my brain veers into deeply grooved HOW pathways.

Obviously, having the know-how is useful. It can be an asset, plus it’s confidence-building. I know how to produce a podcast in my sleep — woot! I know how to re-organize an entire global IT division without affecting existing SLAs — yay! I know how to sing that ONE Madonna song! 🫢

Knowing how to do things can define us and make us feel competent. But it can also box us into familiar patterns.

Through Dawna’s workshop, I understood that focusing too much — and too soon — on the HOW of things can be limiting. It can prevent us from opening ourselves to serendipity, and we end up missing the magical connection of ideas that our brains have yet to witness.

There are so many ways our dreams can come true. The moment we start insisting on one, we limit ourselves from all the other possibilities. — Mike Dooley, author of Infinite Possibilities: The Art of Living Your Dreams

Insisting on knowing HOW can also hold us back unnecessarily. Often, we only need to know the first few steps — maybe even just the first one—and the rest will follow. Trust in emergence.

Reflecting on my HOW dilemma led me to an interesting discovery.

My insistence on knowing HOW isn’t consistent. I can point to many examples in my life where I’ve gone ahead with nothing more than a declarative: “I don’t know; I’ll figure it out.” So, this isn’t a hard and fast rule.

It appears that the HOW becomes a requirement when I’m skeptical and not fully sold on something. I also insist on it before making a big investment in time or effort. In these situations, it probably makes sense and is not entirely a bad idea.

But I now see that I pull out the HOW card when I need to feel in control of a situation. The more insecure I feel about something, the more I need to know the steps, the plan. It also comes on strong when I feel the need to prove myself.

For many of us in midlife, the need to know HOW stems from years of being in control and responsible for significant aspects of our lives and careers. This control can become a security blanket, something we cling to for a sense of stability at a time when our lives are changing so much.

Letting go of our need to know HOW is terrifying… and also liberating. Ignoring the urge to wrap ourselves in our security blanket of HOW is bold. It is a beautiful demonstration of the trust we’ve built in ourselves through the years of leaping and spreading our wings.

Trusting emergence

I’m writing this not from a place of knowing but from a place of trusting. I haven’t figured out the HOW of this. I’m going to trust that with awareness and practice, I’ll figure out the right balance.

For now, I will simply notice when the HOW requirement shows up for me. What’s going on beneath the surface that’s making me feel the need to secure my knowledge of something? I’m also going to try a different question that Donna suggested. Instead of “How do I do this?” ask, “What do I need to know about this?”

How strongly do you feel the need to know the HOW of things before you can commit? When does it show up for you?

🏷 Managing Change & Transitions

💭 muse

“Sometimes, a mistake is the only way of arriving at an original concept, and the history of successful inventions is full of mishaps, serendipity, and unintended results.” — Shaun Tan, artist, writer, film-maker

👤 a midlifer in profile

While she was in university, Laura Izzard had the opportunity to study abroad — an experience that changed her outlook on life. Today she encourages everyone to travel or study abroad. “There is something about travel that takes us out of our comfort zone and places us in a position to view the world with new eyes.”

Read Laura’s profile here.

🍹 reader shout-out

Cheers to WAGO reader Yvonne Marchese, age agitator, author, and founder of The Age Agitators Club. This community brings together women committed to busting through their Midlife Funk to inspire, support, share our stories, and reimagine what’s possible as we grow older. Learn more about The Age Agitators Club.

💬 last word

I used to listen a lot to Andreas Vollenweider in the 90s and recently rediscovered him on Spotify. I mostly listened to this while writing this edition.

Isn’t it great when you rediscover something you used to love?

Here’s to an easeful week ahead.

Cool Beans,
Lou Blaser