Pencil breaking with the text: Ways we set ourselves up for failure

Ways We Set Ourselves Up for Failure

And what to do instead.

I have spent a lot of time trying and failing at things. Diets, exercise routines, writing practices, journaling, the list goes on and on. Things I said I wanted to do, but when I attempted to do them, I lacked the conviction and self-worth to follow through.

It sounds harsh, but I was setting myself up for failure every time I said I was going to start (or stop) something new. It is like I wanted myself to fail so I could continue in the safety of my status quo. We feel safe there because it is familiar, even though some of the time, status quo is the least safe place we can be.

While we live in status quo, we are in our comfort zone. That comfort zone might make us feel terrible, but we still prefer it to the unknown. Terrible is known and therefore safe. Change is uncertainty. What if we do all this work to change something and things get worse than terrible. Or, what if we do all this work and nothing changes at all.

It is completely cliché, but what if we do all this work and change happens for the better? The problem with change is we have no idea what will happen. But change is inevitable, so even if we do nothing, things are going to change.

We make the decision that we are going to make some changes, but often we sabotage ourselves before we even get started. What follows are three things I’ve done and witnessed other people doing, so they seem to be common stumbling blocks to making changes.

We try to make too many changes.

Once we decide to make changes, we just want to jump in and start radically changing everything. This might work for some, but for the majority of us, too much voluntary change all at once overwhelms us and keeps us from wanting to do any of it.

For example, when I would try to “be healthier,” I would say I am going to eat healthier and start exercising every day. When I would inevitably fail by not exercising one day, I would throw up my hands and say the entire day is ruined, so might as well eat a big bowl of ice cream with all the toppings. Or vice versa, if I ate the big bowl of ice cream, then I cannot work out that day. I’m too full!

I’ve decided that since I failed at one thing, everything must be abandoned. Then, the next day I say, well I already messed up this week, so might as well give up for now and I will try again later.


Decide on doing one thing. If you want to start eating healthier and do a daily workout routine, choose which one you might be most likely to stick to and do that. Add the other in later, once you are comfortable in your new routine. If your two changes are connected (like eating and exercising), perhaps you will naturally fall into the routine of the second change. I have seen this in my own change work.

We try to change too much.

This section is related to, but different than, the first point. Just like we can try to make too many changes at once, we also try to change too much. Let’s change the example to developing a journaling habit (because I do not want this to be about diets and exercise, you can read why I even hate the word diet here).

If you aren’t already used to writing every day, then you decide you are going to wake up and write four pages every morning when you wake up (a la The Artist’s Way), that’s a lot. It doesn’t seem daunting when we decide on the change, but when we sit down to write the pages and the words don’t flow, so it takes much longer than the time we thought it might, we give up. Taking that much time every morning is too overwhelming, we have to get up too early, so we quit.  

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Perhaps we don’t begin with four pages of hand-written journaling each morning. Maybe we start with five minutes. As we get used to sitting down and journaling each day (whenever you can because it doesn’t have to be in the morning), then we can expand our sessions to longer times or more pages. Incremental changes will build up over time and after a few months, you will be able to look back and  see how far you’ve come.

We don’t start immediately.

When we decide to make a change, we often say we will begin doing it on Monday, or the first day of the month, or (most famously) the first day of the year. We put the change on the calendar and decide that is the day. The big day that change will happen. In the meantime, we are dreading that day because we don’t want to make changes. We don’t like change as a general rule, even if it is a change we want to make.

We go about our days until the Big Day thinking about how many days of freedom we have before we tackle our change. Oh gosh, only two more days until I have to start exercising. Only one day until I have to get up early and journal for an hour. We dread the big day. This dread is a constant companion and feeds our minds about how much we really don’t want to make this change. We are talking ourselves out of it before we even start.


Once you decide to make a change, just do it. A big ceremony around the change by selecting a date on the calendar only makes it more intimidating. If you slip into it, you might not even register that you are doing something different. If you want to start walking, start right now. Close this article and go. Then tomorrow, go walking again. If you miss a day, start again the next day.

Voluntary changes are not all or nothing, though we tend to see them that way – myself included. When I started recognizing these patterns I discussed above, I started making changes little by little. Doing one small thing and then another, until I started seeing the culmination of my changes.

I also forgave myself if I messed up along the way. Another danger of the all or nothing mentality is that if you are imperfect one day or miss a day altogether, you give up. I know I did. If I didn’t do it perfectly, then there was no reason to keep going – that day or any day. When I learned to forgive myself for showing up imperfectly and keep going, that is when I started noticing all the changes I was making start to shine.

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