This August, I had big plans. I was going to take the entire month off work. I know,  I know! It’s a complete privilege to even consider doing this but it’s one of the few perks you get when you run your own business.

Earlier this year, my business manager, Lauren, challenged me to do something I didn’t think was possible.

She urged me to take the whole month of August off. 

She knew we had the team in place to keep everything running smoothly, and this time away would allow me to focus on being with my family and give my business the creative whitespace it needed.

When we first discussed it, I quickly dismissed the idea. The thought of taking an entire month off felt impossible. My Type A tendencies were screaming at me.

I tend to think that stepping away from work will lead to a massive backlog, reducing my efficiency. 

The idea of slowing down doesn’t come naturally to me. 

If I’m honest, there’s often a lingering guilt or anxiety when I take time off—I feel like I haven’t achieved enough to ‘deserve’ it.

Then there’s my strong sense of responsibility and conscientiousness. I tend to feel personally accountable for everything that happens in the business, which makes it even harder to take time off.

But then, something shifted.

I realised this summer could be the last one where my son would still be excited about going on adventures with me and his 6-year-old sister. He starts secondary school this year, and after this year, he’ll want more independence and will likely prefer hanging out with friends. 

The thought of missing out on this time made me rethink things.

So, I decided to take the plunge and commit to taking August off.

Except… I messed up.

While I managed to turn down all the leadership development facilitation work that came my way, one of my derailers kicked in.

Before I knew it, I had coaching sessions scheduled across most days in August.

Are you familiar with the term derailer?

A derailer is a characteristic or behaviour that, while often helpful in driving success, can trip us up if we’re not careful. 

These are the aspects of our personalities that work for us in certain situations but can become counterproductive when left unchecked. 

For example, being highly conscientious can make us detail-oriented and responsible, but it can also lead to overcommitment or burnout when it prevents us from stepping back. 

In short, derailers are the parts of ourselves that, if not managed, can take us off course from our goals and wellbeing

And that’s just what my derailer did.

In this case my derailer of being over-optimistic.

I know that being overly optimistic can get me into trouble.

I squeeze too much in my diary.

I leave too late . It started with saying yes to just one client, thinking, “I can easily squeeze in a coaching session—it won’t take much time out of my diary in August.” 

Then I said yes to another. And another. 

Before I knew it, my diary was filling up faster than I expected. 

My overoptimism caused me to underestimate the impact these sessions would have on my time, and suddenly, my plans for taking the month off slipped away. 

What seemed manageable in the moment quickly turned into a packed schedule, derailing my intention to disconnect fully.

But, here’s the thing—when I get messages like the one I received from a client over the summer,  I’m reminded why I didn’t say no.

Many of my clients are navigating demanding professional and personal lives, and coaching is their opportunity to catch their breath, reflect, and reset.

So, while I didn’t quite manage to take a full month off, I’ve found a way to support my clients and spend time with my family.

So it turned out to be a win-win… even though I messed up.  

Even though my derailer took me completely off track from my intention for August – luckily, it worked out ok in the end.

But if we’re not careful our derailers can get us into trouble.

Do you know your derailers? 

Those tendencies that can subtly sneak in and throw you off track? 

We all have them, whether it’s overoptimism, perfectionism, or taking on too much responsibility. The key is being aware of them so they don’t end up sabotaging your plans and intentions. 

How do you keep yours in check? 

It might be setting clearer boundaries, learning to say no, or simply pausing to assess the real impact of your choices. 

I know Lauren will be helping me to keep my derailer in check as we plan out next summer for my business!

Whatever it is, recognising your derailers is the first step toward making sure they don’t derail what truly matters to you.