Why You’re Failing at Dieting (and What You Can Do About It)

image courtesy of Thrice 18/3

You’re failing at dieting because you’re making it suck, and what you can do about it is make it not suck.

I could go all Seth Godin on you here and leave it at that, but you’d be like, “Hi. Unhelpful.” So here’s more:

In December, John and I traveled to my hometown in Indiana to spend Christmas with my family, including my two favorite dieters: my mom and dad. They, like so many other Americans, have started and stopped countless diets over the years, and let me know during our visit that they’re giving it all another go in 2013.

I love my parents with all my heart and it would make me so fuggin happy if they’d make healthy changes. I returned home from the holiday with all kinds of diet-related notions swimming in my head–things I wished I could be there to explain to them and remind them of every day as they worked toward a healthier lifestyle.

A couple of weeks ago, I sat down, organized my thoughts, and created a “Keys to Dieting Success” document, which I snail-mailed to them.

This post is inspired by that document.

Ways You’re Making Dieting Suck, and What to Do Instead

Dieting blows, but we make it way more miserable than it actually has to be. Here are four dieting obstacles you’re creating for yourself, and how to get past them:

1. You’re Being Too Strict

Don’t get all ambitious and set these ridiculous diet rules for yourself (no carbs ever, no sweets ever, 1200 calories a day only) that ensure failure. People have a finite amount of willpower. That’s important for you to understand. Eating a diet that’s so inflexible–or just plain isn’t enough food–is awful and impossible to sustain long-term. It feels like punishment. Do you like punishment? Would you keep at it, given the choice (which you have, since it’s self punishment)? Right.


I suggest you cut out nothing. Don’t eliminate anything from your diet, just add a million new healthy things. Start with lots of water, a multivitamin, and fish oil supplements–how easy is that? Now add crazy amounts of vegetables. At every meal or snack, load up on produce. Then we’re gonna add protein, then we’re gonna add healthy fat, and so on… You’re just crowding out the bullshit, you see? Nothing is off-limits; you’ll just eventually run out of room for the bad stuff.

2. You’re Focusing on What You Can’t Have

When people start a diet, all they think about is everything they’re no longer eating. This is dumb and a form of self-sabotage.


No matter if you’re trying to get healthier or smaller or leaner, there are going to be plenty of items you can and should add to your diet. This is kind of fun and should be your focus. Every time you notice you’re feeling sorry for yourself because you “can’t” have something (which, if you’ve implemented my first suggestion, shouldn’t be an issue anyway), make a mental switch to consider what you can have. It’s a lot.

3. You’re Trying to Make Changes That are Too Big

You’re not going to go from fast food every night to washing, chopping, and steaming fresh veggies and grilling steaks for every meal. I mean, you’ll do it for maybe a couple of weeks, but you’ll quit, because that way of living is way different and way more labor-intensive than what you’re used to. You’re already dieting, and now you want to make your life suck a little more by using precious free time to prepare this diet you’re not even jazzed about? Stupid. Recipe for failure.


Pay for convenience. Pay for pre-washed and pre-chopped produce. Pay for rotisserie chickens. You need to pay for these things, because you’re not going to routinely do all this. This is a cost that’s 100% worth it–when you really think about it, don’t you agree? Pay for convenience now or pay for medical bills later. Stop kidding yourself, and start supporting yourself.

4. You’re Not Replacing Satisfaction

Eating is so, so satisfying. And we eat for all kinds of reasons other than hunger, because it satisfies many needs. If you’re doing this–and so many of us are–you’ve got to find a way to replace that satisfaction before beginning a diet plan. Otherwise, you end up unprepared for the moment you want to pop a cupcake because you’re frustrated with an assignment or can’t take the afternoon nap your body’s calling for or are just bored and it’s your default reaction to grab a snack, or whatever, and you either feel the unpleasant void of not eating and eventually give up after you feel it too many times, or you give up right away and call it another failed diet.


Decide on some alternative sources of satisfaction you’ll insert in place of eating. If you’re a calorie counter, just the act of tracking itself is satisfying, and it keeps you from rationalizing food you don’t need (this is true–and a really powerful tactic–for me). Other good eating replacements are:

  • simply taking a moment to soak up your own badassery for committing to making these changes in the first place,
  • reminding yourself of that awesome feeling you have when you get in bed for the night and realize you totally lived this day like a healthy person,
  • dreaming up a sweet (not literally) lunch you can pack for yourself tomorrow, or
  • browsing Pinterest for healthy meal and snack ideas.

OR, you can do something totally unrelated and just chill on your couch with a book, or watch TV with zero guilt. Satisfying and calorie-free.



What do you think sucks the most about dieting? What has caused you to fail at dieting in the past? What has helped you succeed?

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Your thoughts?
  1. Kate says:

    I think what sucks most about dieting is the notion that it is something to be endured. You just have to eat nothing but celery and cottage cheese for six weeks and you’ll lose 10 pounds! But after those six weeks, you go right back to your old eating habits and put the pounds straight back on. Diets aren’t sustainable and don’t create lasting change in your eating habits.

    I also really hate the strictness of dieting. One little slip up and you feel like you’ve blown the whole thing so you may as well finish off the rest of that tub of ice cream…

    • Cassie says:

      Great points, Kate. It’s funny, I resisted the word “diet” for years because all the things you just said are completely true of traditional diets. I use the word here (and in everyday conversation, now) because the overall goal of weight loss (should be “fat loss”) and eating better is much more commonly called dieting than anything else, and sometimes I try to ignore the “right” way to say something in favor of using words that help me better connect with an audience/people I’m talking to.


      Yes, the notion that a healthier way of eating is something that must be “endured” is SO misguided. It doesn’t have to suck, and you don’t have to be hungry. The original document I wrote included something like “You should never be hungry! You should always eat something if you’re truly hungry.” The key here is recognizing the difference between true hunger and appetite. (I have a post coming up about this…)

      And oh yeah, the strictness–it’s the all or nothing mentality and a HUGE issue for me that I’ve mostly overcome but still pops up occasionally. I’ve found mentally stepping outside the situation and considering how ridiculous I’m actually being helps. In the document, I told my parents this was not a diet, just a healthier way of life. And you can’t “go off” life! I told them, I don’t care if you eat the whole kitchen, you didn’t go off something, because you’re not on something. You’re just living life, and these things happen in life, and now you’re just going to keep living life…and eat a little better next time.

      Thanks for your thoughts, Kate!

  2. Crystal says:

    I love that you snail mailed this info to your parents! Very caring.

    What always messes me up with “dieting” or just eating healthier in general is thinking about food too much. Dreaming up what I’ll make for lunch and browsing for healthy meal and snack ideas trips me out and into thinking I’m hungry RIGHT NOW. Also, extra time chopping and cooking means extra time thinking about food and planning to have enough time to cook it. I think about how I have to make sure I get enough calories and then always end up eating way more than I normally would. Food becomes an all consuming obsession when it normally isn’t for me.

    • Cassie says:

      IDK why I snail mailed it really…I think I was imagining them hanging it on their refrigerator. 🙂

      Oh yes, food can so easily become an obsession when dieting. The five years I spent struggling with anorexia and bulimia speak to how much I feel you on this. I actually have OCD, so obsessing over something is literally natural for me. What helped for me–and actually, what was key to my recovery–was rechanneling my energy/focus/obsession. Instead of trying to be the skinniest I could be, I started trying to be the healthiest I could be. Instead of focusing on calories, I focused on nutrients. Instead of focusing on NOT eating, I focused on eating like a “normal” person…and so on. (Totally planning an ebook on this method of recovery, BTW.)

      Maybe redirecting your focus could help??

      Thanks for your comment, Crystal!

  3. Sarah says:

    One major help to me was changing my brain to stop the “last meal” mentality every time I ate. I had to tell myself over and over again that I didn’t have to eat the entire plate. That I would have plenty of chances to eat that food again. And that eating a specific food or amount of food would not improve my life in any signifigant way, but being healthy would.

    • Cassie says:

      “That I would have plenty of chances to eat that food again.” Oh, this is HUGE. This is most helpful for me at night, when I’m struggling to find a stopping point at dinner. Sometimes I’m like, Dude, Cassie, you get to eat breakfast in the morning, and you’re not going to wither away in starvation over night. I need to use this strategy more, actually. Thank you for the reminder!!

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