3 Sneaky Ways You Might Be Self Sabotaging (Without Your Knowledge)

Alexis Haselberger
6 min readAug 28, 2023


Photo by Pavel Danilyuk

Sometimes, you don’t act in your own self-interest. Sometimes, you self-sabotage.

If you’re lucky, you have some awareness of when this is happening. You can do a little post-mortem.

And, next time, you can make a different choice.

But sometimes, you engage in behaviors that are just a little bit sneakier. At first glance, they seem harmless. Or worse yet, these behaviors might actually seem helpful. But they’re deceitful.

They keep you confused.

So you keep doing them, and you keep wondering why you feel stuck.

The behaviors are tricky because they are natural instincts.

Most of the time, I believe in “follow your gut.” But not here.

What are these natural instincts dead-set on doing you in without your knowledge?

Let me pull back the curtain and let you in.

And as you read on, I want you to think about whether you can identify these behaviors in yourself.

1) You agree to, or even suggest, best case scenarios timelines

  • What this looks like

It’s Wednesday. Someone asks you to do something. You want to look good. You want to impress them. You’re an optimist. You think (or wish, or hope) you can get this thing done by Thursday. So you say “I can get that do you by Thursday. Does that timing work for you?”

They say “That’d be great; thanks”. And you both go on your merry way.

You start working on this thing and you realize, “uh oh, it’s a little more complex than I thought”. Or something more urgent than this gets assigned to you.

Or both.

And, now you’re left with 3 choices, none of them great: Miss the deadline, ask for more time, work late into the evening to get it done.

  • Why it doesn’t serve you

When you do this, you’re over-indexing on the good feeling of telling someone you can get it done quickly. But this leaves you without any buffer. If there are delays for any reason, you can’t absorb them. You’re trading the short term goal of looking good in the moment for the long term goal of being accountable. You’re choosing optimism over realism. And it doesn’t pan out that way hoped. So in the end, you lose.

  • What to do instead

Give yourself buffer. If you think you can get the thing done by Thursday, say “I can get that to you by next Monday; does that timing work for you?”

Give yourself the gift of not over-commiting.

Look, none of us can see the future, but two things are for sure: 1) most of the time, stuff come ups, and 2) stuff takes longer than you think it will.

Plan for that! Agree to that! Bask in the glory of giving yourself enough time to do the work.

  • What I hear you saying in your head

“But I want people to think I’m fast, and good!”

Look, I get it! But let me tell you something else. I’ve managed a lot of people and I’ve had a lot of colleagues and I’ve always preferred working with folks who did what they said they would, by when they said they would. I prefer a realistic answer, even if it’s not as soon as I would like it to be done.

Because you can’t plan around optimism.

2) You don’t capture new tasks, or document what you’ve done, in the moment because you “don’t have time” or you’re “too busy”

  • What this looks like

It’s a busy day. You’ve got a lot to do. Soooo many things on that task list. So you just get cracking. Requests are coming at you left and right. Meetings are back to back. You don’t have any time to add new tasks to your task system. You don’t have time to update the tasks you made progress on or completed. Then you get to the end of the day, look at your task list and think: “I’ll update that tomorrow”.

It’s tomorrow. You think about updating your task list, but that’s going to take a lot of effort, because stuff is showing up now as “overdue”. And you don’t quite remember what happened yesterday, so it’ll take some look through your emails and jog your memory. And you’ve got more assignments, more meetings, more emails, more Slack messages.

  • Why it doesn’t serve you

When you don’t add tasks as you go, or update your task list as you work on a task, you’re ensuring that when you do update, it’ll take you longer to do so, and that you’ll undoubtedly find that some tasks have fallen through the cracks.

Yes, it FEELS like you don’t have time to update in the moment.

But the reality is that you don’t have time NOT to. If you don’t do it now, you’ll pay for it later, in extra time and extra stress.

  • What to do instead

Keep your task list open ALL THE TIME. When a new task comes your way, add it. When you do a next action related to a task, update it. It’ll take between 10 and 30 seconds now, but so much longer later. Why? Because you’re thinking about it now, you’re in it now, there’s no recollecting what you need to do, there’s no research to remember where you left off. Think about your future self.

3) You abandon your systems when things get busy

  • What this looks like

Let’s take the example above and take it to the next logical conclusion. You’re so busy that you’ve abandoned your systems altogether. You think: “How can I possibly justify spending any time maintaining my system when I have so much real work I have to do?”

So your system fades into the background. You’re swatting at tasks furiously. You batting away the small ones, but there are just so many. You think “When I take care of this queue of little items, urgent items, squeaky wheels, I’ll get to the big important stuff”.

But the little stuff never stops coming.

Now, it’s been a few weeks. Everything in your task list is overdue. Your brain is packed to the gills with swirling thoughts. You know you’re missing something. But you’re not sure what it is or when it will come back to bite you in the ass. Your system has gone to the graveyard of abandoned task apps and you feel like you might keel over too.

  • Why it doesn’t serve you

While it may FEEL like the best thing you can do is just start working, responding to whatever comes your way, abandoning your system ensures that you’ll miss things. And that what you do will be reactive in nature instead of proactive.

This means that even if you’re working just as hard, or even harder, it’s very likely that your efforts are not moving the needle.

You can’t do everything. So deciding WHAT to do is perhaps the MOST important work you can do. And when you use your systems, you’ll be ensuring that the things you do today are more important than the things you don’t do.

And you’ll feel less stress because you’ll know that you made the right decisions and that when you didn’t do something, it was on purpose, because you did something else that was more important or impactful

  • What to do instead

When things get busy, resist the urge to abandon your systems. When things get busy, double down on your system. Any work you put into maintaining your system will come back to you in spades. The ROI on your task system is out of the park.

Have you been nodding along? Have you identified these behaviors in yourself? Perhaps you’re thinking “Yep, that’s me”, but you’re not quite sure you can make the changes you need to make on your own?

Well, you’re in luck! “Time Well Spent: Time Management for Real People”, my group coaching program, is open for enrollment from 8/29/23 to 9/7/23. And if you’d like to make some change, but you need a guide to get the results you want, I’m here for you.

I currently offer this program twice a year, so now’s your chance to enroll!

Subscribe to my newsletter HERE.

Originally published at https://www.alexishaselberger.com on August 28, 2023.