Self Sabotage and why we do it!

Bay Street in Toronto after delivering a Change Management session for the Purpose & Sustainability Team at Gore Mutual Insurance.

A Monthly Newsletter: August 2025

Welcome to the August edition of my monthly newsletter! This month and week, I have been reflecting on patterns of behaviour that I have noticed in myself and then also show up for my clients. It’s the stuff that we often can’t see ourselves, (our blind spots) but are obvious to others! Self sabotage is one that comes up frequently but is often hard to spot. In this issue I dig into this a little and provide some resources that can help.

Would love to hear your feedback on this one!

🧠 How We Get in Our Own Way (And What to Do About It)

Unpacking self-sabotage, one quiet habit at a time.

Have you ever felt like you’re finally making progress… only to somehow derail yourself?

You miss a deadline. You procrastinate. You hesitate to speak up. Or you tell yourself, “I’m not quite ready yet.” It’s subtle, but it’s powerful: self-sabotage.

Lately, I’ve been reflecting on the quiet ways we can hold ourselves back professionally—especially when we’re close to growth or new visibility. It might show up as perfectionism (“If it’s not flawless, I won’t share it”), people-pleasing (“I’ll just take this on myself—again”), or avoidance disguised as productivity.

Sometimes it’s even sneakier. I once delayed sending a proposal to a new client. I told myself I was waiting for the right words, but if I’m honest, I was worried the work might stretch me more than I was ready for. When I finally sent it, I made a few small but noticeable errors—nothing huge, but enough to chip away at their trust. From the outside, it looked like a simple miscommunication. But I knew better. That was self-sabotage.

These patterns are often protective—formed at times when they served us. But in our current roles, they can keep us small. The tricky thing is, we often look like we’re doing just fine. But inside? There’s a lot of second-guessing and noise.

What’s helped me—and many I work with—is simply noticing it. Naming the pattern. Then choosing differently.

If any of this resonates, here are a few resources that offer real, practical insight:

📚 Books to Shift the Narrative

  • The Mountain Is You by Brianna Wiest A compassionate, honest look at why we self-sabotage and how to work with our resistance instead of fighting it.

  • Playing Big by Tara Mohr Especially valuable for women navigating self-doubt in leadership or visibility. Gently reframes what “readiness” really means.

🎧 Podcasts That Dig Deeper

What I’m learning

Self-sabotage doesn’t mean we’re broken. It usually means we’re scared—of being seen, of failing, or of what success might ask of us.

But every time we catch ourselves in the act, we create space for something different: A new pattern. A clearer choice. A gentler voice.

So here’s to spotting the habits that don’t serve us anymore. To giving ourselves permission to show up, imperfectly. And to learning that discomfort doesn’t mean stop—it often means you’re on to something.

You’re not alone in this.

—Emma

Share this with someone who’s overthinking something big right now. You never know who might need a gentle nudge today.

 ps. When you’re ready…..I help leaders and organizations through in-person team training, coaching, and 1:1 virtual coaching. Reach out for a complimentary intro call.

Team facilitation in action!

Did you know I also provide facilitation as well as team training sessions?

Hydel Inc. Leadership Team - Providing 2 days of facilitation at Millcroft Inn & Spa, Ontario

If you are looking for some support for your next offsite strategic session, drop me a message to discuss your needs and to see how I can help.

I find (from my own experiences of working with an outside facilitator) having someone there, to take the pressure off you, so you can participate rather than lead the session, is the key benefit of bringing in an outside facilitator.

Want to learn more? Drop me a message entitled ‘Team Facilitation’ to [email protected]. or book a call here.

Referring Someone in Your Network

It makes sense that you trust your colleagues and friends to provide great professional contacts. So, if someone in your network could use coaching and/or team training support, please introduce us!

My LinkedIn profile for sharing is here.

I’m very grateful for everyone who connects me with their colleagues and friends. Thank you!

Emma