Stop Should'ing Yourself

My friend Nataly Kogan asked a provocative question recently in her newsletter on LinkedIn.

The question?

What is actually guiding the choices you're making in your life right now?

The honest answer to Nataly's question, for most of us, is: should.

"You should take this on"

"You should attend"

Should is sneaky. It may not start out as obligation or fear or someone else's expectation, but it frequently morphs into that, insidiously showing up on your calendar, week after week, sucking your time, mental bandwidth and energy — and it will continue to do so, unless you challenge it.

Whose Urgency Is This?

In The Social Billionaire, I prod readers to challenge their shoulds by taking a good, hard look at their calendar, and all that is commanding their attention, so they can identify the unchallenged shoulds derailing their actual wants and needs.

Most of us have at least one commitment sitting on our calendar that is way past its due date. You know the one. It's the committee you've mentally resigned from seventeen times or the recurring daily stand-up meeting on a project where your skill set isn't called upon. It's the commitment that is still on your calendar because "they need me" or "it would look bad" (or some other variation) prevents you from moving on from it - but you resent it for still being there on your calendar, regardless.

By not resigning or saying no or stepping back, you're capitulating to the should.

What Lights You Up?

Nataly is very vocal about her career burnout - before she was a best-selling author and speaker, she was a successful tech CEO who burned out because she kept ignoring what energized her. 

In the pursuit of external metrics of success, we too often ignore our internal compass.

I spent years as a lawyer who was respected, capable, and not particularly lit up by the work (truth be told). I questioned that career path when it was well past its expiration date. Career clarity ultimately came for me in my 50s, not at 22 — and I've stopped regretting that timeline. What I know now is that the pause to look at how I spend my time, taking a moment to reflect on what actually energizes me is essential.

And it starts by taking a hard look at what goes on my calendar.

What are your wants? The real ones. The ones your soul is screaming for.

Here's a 15-minute exercise for you. Look over your calendar commitments from the past week or two. Then with brutal honesty:

⭐️ Star what nourishes you.
❌ Put an X beside what drains you.
🔦 Highlight what only you can do.
⭕️ Circle activities you’ve told yourself you "have to" do.

What you're left with is a should-to-want ratio — and it's almost always more lopsided than is necessary (or helpful or healthy).

Flush the shoulds and create a calendar you want:

🗓️ Schedule the wants. Give them place of priority in your calendar.
🚷 Delegate or ditch the drains. Ditto for the "have to's".
🚧 Park the "could be good" opportunities in the not-for-now corner.  

This flushing the shoulds exercise is about you being honest about the time you actually have, and hyper-intentional about where you choose to direct it, as there is a choice here. A choice to honor the want or to defer to shoulds. Which do you choose?

📘 The Social Billionaire: A Networking Roadmap for Women Seeking to Flourish and Achieve More is available in paperback (workbook) format on Amazon + Barnes & Noble and in ebook on Kindle, Bookshop.org, Smashwords, Vivlio, Thalia, Apple Books, Fable and Rakuten kobo.

📚 Conference. event, offsite, team building? For bulk orders, place your order here, on IngramSpark. Personalized copies (yes, you read that right) can also be ordered via IngramSpark.

💡 Book reviews help other readers find the books they should be reading, and I'd love ambitious women to get the networking strategy they need. Review The Social Billionaire on Amazon and/or Goodreads.

🗝️ If you’re planning events designed to boost women’s professional connections, let’s talk, as I’d love insights from The Social Billionaire to be part of these conversation.