Why is saying no so dang hard? I’ll give you the short answer first.

According to The Enneagram Institute, Type Twos are defined as being “generous, demonstrative, people-pleasing, and possessive,” known for slipping into “doing things for others in order to be needed.” Our greatest fear is being unwanted or unworthy of being loved, and our greatest desire is, well, to feel loved.

This stuff isn’t new, per say, although I have enjoyed getting to know the Enneagram test in more depth lately, thanks to some of the authors I follow. What’s new is realizing just how chronic this “yes” decision-making posture is for me.

Maybe you struggle with it, too.

Have you ever had someone ask you to do something, felt flattered and then compelled to say, “Yes, of course!” only to instantly regret it? Your internal conversation goes something like this: Why the heck did you just agree to that? You know you’re already over-committed. Now what are you going to tell them? I can’t tell you how many times I have this conversation with myself, and it’s only the past six months that I’ve started to anticipate it.

Two years ago, I read Lysa TurKeurst’s The Best Yes: Making Wise Decisions in the Midst of Endless Demands. It moved me. Convicted at how I’d been living “at the mercy of other people’s requests,” I decided to make a crucial change in the way I approached time management. Heck, this was the sort of thing I was supposed to be teaching our students in the Learning Commons. Why was it so ridiculously hard to say no?

Trust me, it’s not because I’m Wonder Woman. I wish. It’s just that I have about a billion different interests, and I tend to make that pretty public. So people ask. And I say yes.

The chronic pattern got born out of survival, when I lost my job two years ago and had to start saying yes to any job I could lay my hands on (at least that’s what I told myself at the time – perhaps the jury’s still out on that one). Still only making part-time income, I’d committed myself to the following jobs:

– Freelance academic editing
– Teaching swim lessons
– Working as an admin at my church
– Interning for The Gray Havens
Teaching Writing Boot Camp at WJU

Of course, I was beyond grateful for all these opportunities, as they helped me pay the bills. But that summer began the habit of saying yes without thinking I had the choice to say otherwise. Sure, I can do a lot of things sort of well. But instead, I want to do 1-2 things excellently.

In fact, I only want to do what God’s called me to and what he’s uniquely built me for. This isn’t always possible because sometimes we can’t be picky. But, if I have the choice, I want to be so rooted in my identity that I feel confident saying no to perfectly good things in order to say yes to the best things. The best yes. 

So, is there hope for an Enneagram 2?

What’s important for us to remember is that our empathy and outward-focused people-pleasing activities can and surely will lead to exhaustion. We’ve got to be wise. With only so many resources, if those are depleted, it will take more than a little self care to recuperate. But it’s more than even this. What sort of people do we really want to be? No matter how many amazing opportunities there are, I only want to say yes to my greatest calling. True, my mind is usually explosive with ideas, but maybe God has called me to be the Visionary and not always the Executor — the Networker, but not always the Director. Maybe stepping outside of my designed role, my strengths, is actually not just exhausting but disobedient.


This fall, I find myself in a familiar place. On top of my day job, I’ll be teaching two college classes this spring (which I truly am excited about), as well as continuing to freelance edit for a friend and somehow try to finish my book manuscript. But, to be honest, there’s also a lot going on beneath the surface. I’m taking steps to heal and protect my mental health, my physical health — things I know I have to face before ever fully moving forward into the life God has for me. These things take time and energy, too. Sometimes even more because of deep-seated emotional and spiritual layers. I have to have a boat load of grace and compassion on myself during the slow process, while trying to juggle everything else.

So, where does this leave us?

I want to be a healthy Type Two — make that a healthy person: “Someone who sees [people] as they are, understands them with immense compassion, helps and encourages with infinite patience, and is always willing to lend a hand — while knowing precisely how and when to let go.”

Hopefully it leaves us a little wiser for the journey, and a lot more resolved to say yes to what actually makes us come alive.

[I highly recommend checking out the nine Enneagram types. It has been hugely insightful and encouraging for me to discover why I’m motivated to act the way I do and what healthy ways I can grow and develop. Beth McCord of Your Enneagram Coach guides people in how to use this test as a tool to better understand how to live uniquely in light of the gospel and our identity in Christ. Annie F. Downs has a great interview with her here.]

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Bailey-12  Bailey Gillespie works as Director of Academic Engagement at William Jessup University and is also adjunct faculty. She lives near Sacramento, California and loves connecting with people over health, creativity, and faith. Recently, her writing has appeared on Real Hope Rising, Voice of Courage, and The Rabbit Room. Read more at baileygillespie.com or follow her on FacebookInstagramTwitter, and Goodreads.