I am a people pleaser. When someone asks something of me I normally say “yes”. Recently, however, this mentality burnt me. Here follows my story of people pleasing, how I ended up letting people down, and how you and I can try to avoid this situation in the future.
It all started when it came time to arrange travel for a work conference. The company I worked for required that all travel and accommodation be arranged by the “travel” manager. The conference was in the US so being in Australia meant that it was going to be a marathon affair getting there and getting home. My itinerary arrived in my inbox one morning, I opened the email and scanned through it looking for flights, dates and times. It was not long into my reading that my jaw dropped to the ground. The conference was a 4 day event – starting on Monday afternoon and ending on Friday at lunch. My itinerary had me leaving Australia on Saturday and arriving on Monday nine days later. Monday was also a public holiday. To clarify everything here, I was going to be in the US for 6.5 days and miss-out on 5 days worth of weekend, leaving my wife at home to look after our two small kids on her own for the whole time (we don’t have “help” nearby).
Naturally my wife wanted me to take the Tuesday off from work so I could spend a little extra time with the kids after I got home so that they could get to know me again. “Yes”, I said, “of course I’ll do that.”
The week before I was to fly out a colleague asked me to attend a meeting on this same Tuesday. “Yes,” I said, “of course I can help out with that.”
Uh oh… Now two different people, in two different worlds, expect me to be with them at exactly the same time. Not wanting to let anyone down I ignored the situation. So at this point both people thought everything was OK and I was trying to ignore the imminent catastrophe.
Roughly half way through the conference I began to feel the weight of expectations on my shoulders getting heavier and heavier. Something had to give.
The Choice
When faced with this situation it’s obvious that I had to let someone down, but who? Do I tell my wife that I have to go straight back to work after being away for 9 days and then face the immense guilt that followed. Or, do I tell my colleague that I’m not going to be able to make it to the meeting. The latter option sounded easier, however, my colleague wasn’t at the conference. Instead they were on leave in another country altogether and wouldn’t want to reschedule the meeting while away. Turns out, that meeting was hard enough to arrange in the first place, so for me to just abandon it would be terrible.
What to do? In the end, I stuck with my wife. My reason being that family is forever and always comes first. Now I had to somehow break the news to my colleague. Being in two very different time zones I had no choice but to use email. This proved to be a challenge. Tone and intent is very difficult to portray in text, even with those delightful emoticons. I tried to be as diplomatic and apologetic as possible in my email, but of course it doesn’t really matter if the email doesn’t get read. Which it didn’t.
Nevertheless, since I had sent the email I had subconsciously absolved myself from the situation. I’d committed to my wife and was now “free” from other commitments.
Wrong.
Later that Week
Eventually that imminent day finally came. You know the day – it’s the one where everything you’ve worked so hard to avoid and delay comes back and lands on you like an anvil on a coyote. It hurts, bad.

I was spending the day with my family, hanging out and just enjoying their company. We were out for a walk when my phone rang. I recognised the number as the office, but couldn’t tell who. “Hello” I said and then I began to realise the gravity of the situation I had created – how important it was to both my colleague, their manager, and the client, that the meeting I had avoided went smoothly. The email I had sent during the previous week was only just read. There was no backup, no alternative and no other plan. The meeting was going ahead. I had unintentionally given everyone the finger regarding the meeting. My actions said to everyone that I just didn’t care enough, even though my intent was far from that. That phone call, the anvil, was followed shortly by an email from my manager. It’s not often that I cause this kind of negative impact, but when it does happen it hits me like a slap in the face. I guess the positive outcome is that I resolved to do everything I can to avoid the same situation while being as helpful as I can to everyone.
It is ironic that by trying to please everyone I had in fact let people down, and ended up feeling incredibly guilty and angry at myself. How could I have let this situation occur? I’m better at managing my time than this, surely?
Timing is EVERYTHING
I have come to realise that timing is everything when it comes to setting expectations. Here’s how the story should have gone.
As soon as I received my itinerary for the trip and I’d told my wife, and straight after she asked me to take the Tuesday off I should have marked it in my calendar and let my manager know my intentions. This woud have then superseded the invitation for the meeting and alternative arrangements could have been made with time to spare. Instead, I was invited to the meeting before I was able to arrange the day off. I said “yes” not wanting to disappoint anyone, chaos then occurred and I ended up letting down my colleagues and myself.
Recovery
So far I’d managed to dig myself a giant hole, jump in, and then kept digging down. Not ideal. The only way I had to recover from this situation so that I could be looked at in a good light again was to apologise, plain and simple. To take responsibility and ownership. They say honesty is the best policy and I’m a firm believer in that. I spent quite some time thinking about this and about how I would approach my colleagues. I eventually decided that it would best be received if I talk to each colleague individually. That way they could express their personal concerns and I could do my best to grovel apologise.
First I asked to have a quick chat with my colleague’s manager. There’s absolutely no doubt in my mind that this person was made aware of my decision to not go to the meeting, but even if they weren’t aware, a preemptive apology would be seen as an act of honesty and sincerity and would show my intent to not make the same mistake again. And so I began, “as you probably know, I stuffed up the other day. I wanted to say how sorry I am for how I handled the situation. I know exactly where I went wrong and I’m taking steps to make sure it doesn’t happen again.” Apology accepted. Next, I made an effort to continue the conversation, changing the subject and the tone to something a lot more positive. Doing this meant that we both walked out the room feeling positive and with the past behind us.
I then used exactly the same approach with the colleague that I directly impacted. The end result was that the two people that were most impacted know that I have taken responsibility for the problem and that I’m going to make sure it won’t happen again.
How you can avoid this and other similar situations
Scheduling and arranging your activities as early as possible is key to keeping people happy. By scheduling activities, and days off, in your calendar as soon as you possibly can you’re offloading the burden of taking on too much. Basically the responsibility of saying “yes” or “no” to people is removed from you and given to a system that can’t be argued with. Sure you might get asked to shuffle your calendar around, but that just means that whatever was in there first is moved, not removed. You’ve allocated time and time is the most valuable thing we have.
Honesty goes hand in hand with successful scheduling. Being honest with yourself and others about how long a certain activity will take will avoid clashes and overlap with meetings and family time. Imagine that you’ve committed to a meeting that’s been scheduled from 4pm to 6pm and you’ve also committed to dinner with family or friends from 6pm. Clearly something is going to give. What happens is that the meeting doesn’t get your full attention since you’re stressing about making it to dinner on time and then when you do get to dinner, you’re late and you’ve possibly caused some problems with everyone, not to mention the amount of guilt you could end up feeling.
By being honest and using scheduling properly and early you can go along way to avoiding the same embarrassing situation I ended up in. If you’ve ever been in a similar situation to my story what did you do to make amends with everyone affected and what measures did you put in place to avoid the situation in the future? Share your own story in the comments below.
