Key Takeaways From How To Walk Into A Room

I tabbed + highlighted a ridiculous amount in Emily P. Freeman's latest book. Here are a few of my takeaways.
Christi Hegstad April 14th, 2024

When I first saw the title of Emily P. Freeman’s newest release, How To Walk Into A Room, I assumed it was a book about confidence. And while I read abundantly on the topic of confidence, I wasn’t in that mode at that time.

Fast-forward a few days, when I stumbled across one of Freeman’s Substack articles and encountered this line:

“Just because you’re good at something doesn’t mean you have to do it forever.”

Consider me intrigued.

After a bit more reading, I came to discover I made a wrong assumption about her book’s focus. Rather than being about confidence (although that may play a role), this is a book about making decisions.

Specifically, deciding when to stay – in a situation, relationship, or job, for instance – and when to walk away.

In the midst of making some significant decisions myself, I am not exaggerating when I tell you I hopped in my car and drove to the bookstore that very day, purchased the book, and devoured it within 48 hours. This was 100% the right read at the right time for me, and I will certainly revisit it going forward, too.

The General Premise

Upon reading a chapter or two, the title of the book made complete sense: Freeman suggests we view our decisions as rooms that we enter and exit throughout our lives. Many of those rooms can and do change over the course of our lives – through choices we make (ie, to move to a new city), choices made for us (ie, the company downsizes and eliminates our job), or life experiences (ie, our children grow up and leave home).

“Our whole life is like a house, and every commitment, community, role, and relationship is like a room,” Freeman writes. “At some point we’ll find ourselves walking into new rooms, leaving old rooms, being locked out of other rooms, or looking around at familiar rooms and questioning if it’s time to move on.”

This metaphor proves incredibly powerful throughout the book as Freeman shares stories, examples, and experiences to portray the changes – ready or not – life brings our way.

She kicks off the book with several questions we may be asking ourselves, such as:

Should I stay or is it time to leave?

How bad does something have to be before I can let it go?

What if I stay and nothing changes?

What if I leave and everything falls apart?

If you’ve been on the planet for a while, you’ve undoubtedly asked yourself questions like these or others Freeman presents. The rest of the book shares considerations for making your decisions with, if not certainty, at least a greater sense of knowing and alignment.

Highlights + Takeaways

If you saw my recent Instagram photo mentioning this book, you also saw the ridiculous number of tabs and page flags I inserted to denote key points. I may as well have simply highlighted the entire book when all was said and done! But here are a few takeaways to get us started:

Ask A More Helpful Question

As a coach, an important part of my work involves asking deep, forward-moving questions. I love that Freeman didn’t lace her book with platitudes or ‘here’s the right decision, here’s the wrong one’ sentiments, but rather she wove in questions to ask yourself. For many of life’s decisions, there is no one right answer; she provides a framework for discerning answers for yourself.

Chapter 2 highlights a list of 10 questions to start, along with a helpful reminder: “It’s vital that you begin this process as honestly as you are able to at this time,” Freeman explains, “so that you can make a decision in alignment with what’s actually true now, not what you wish to be true or what used to be true.”

Consider Your Core Values

If you’ve coached with me, you likely know how important the process of clarifying core values is. I believe knowing and honoring our values is a vital step in achieving goals, envisioning our ideal future, and living life to our fullest potential. Although Freeman is not a coach by training from what I gather (she is a spiritual director and longtime podcaster), she shares a similar emphasis on the importance of core values.

In addition to offering ideas for clarifying your values, she points out the dangers of not knowing them, too: “You could become highly successful in a life you never wanted. You might allow other people’s agendas to determine your yes and your no… You could find yourself saying yes to a lot of great opportunities that lead to someone else’s stage and fulfill someone else’s agenda.” Freeman dedicates a good portion of Chapter 4 to this values conversation.

Allow For Alternatives

‘Do I stay or do I go?’ may seem like the best question, but Freeman points out important considerations here: Such a question “implies a binary, as if there are only two options. This is rarely the case.”

In addition, it implies a one-time, once-and-for-all decision. “In reality, most of our decisions come slowly, are a series of deciding to stay today and again tomorrow,” Freeman says. “Not once and for all, but once for now and twice for later.”

Later in the book, she offers considerations that can ease these implications of finality and binary thinking, such as adding ‘for now’ to the situation. “You might not know for sure,” she gently reminds us, “but you can know for now.”

Endings, Beginnings, and The Hallways In Between

As much as I appreciate this book, I think my favorite aspect is how Freeman so eloquently distinguishes between concepts that we may easily intermingle in our minds. The difference between an ending and closure, for example, or the difference between readiness and timeliness.

I’ve experienced not feeling ready but the time for the change arriving anyway, or vice versa. And I’ve experienced something ending without the benefit of closure. After reading this book, however, I can more clearly distinguish between these experiences – and have words or strategies in my back pocket for navigating through them, too.

Overall, this book has prompted me to think differently and will stick with me longterm, both characteristics of an excellent book in my view.

Have you read How To Walk Into A Room? What did you take away from the book?

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