9 Questions To Ask Yourself When You’re Fed Up With Dieting

Diets are inherently contradictory. They demand you to fit a new set of instructions (the diet itself) into your old lifestyle.

Instead, you should be working toward building a new lifestyle.

Diets promise short-term solutions: “try our 10-day quick-fix, magic elixir, ultra-secret, fat-scorching solution!” Well, that’s great, but what happens after 10 days?

Think of it this way: diets are like cramming for a test. You might pass the test but what did you get out of it? Do you really think that you’ll be able to override an entire lifetime’s worth of habits with a new set of rules in a snap of the finger?

The answer is No. And if you’ve ever tried and failed a diet before, that’s proof.

And yet, that’s what all these commercial diets promise. They expect you to read the manual (the new instructions) and somehow learn how to integrate these new choices and habits to meet your lifestyle. What you’ve found, inevitably, is that life always wins. It’s too hard to cram in this new diet without first changing your lifestyle…which means changing your habits.

If so, isn’t it finally time to try something different? The definition of insanity, after all, is trying the same thing over and over and expecting different results.

If you’re up for it, there are some questions below that I want you to be honest about. They’ll challenge you, yes, but they’re designed to help you.

1. How many times have I tried to lose 10 pounds in 1 month, or 20 in 2?

Let’s be real for a minute. How many times? How many times have you tried dieting? 5? 10? Maybe you’re always “sort of on a diet.” Maybe the past 5 years have been one great big perpetual diet.

OK. You’ve proven you can “diet.” Congratulations. That means you’ve proven diets don’t work.

2. Are my dieting attempts a race against the clock, rather than attempts to learn something?

I’ll say it again and again because it’s my job: the goal is not to lose weight quickly. The goal is to master your diet.

I never talk about cutting portions, reducing calories, or hopping on the scale every morning to track how much weight you’re losing. I talk about changing the kinds of food you’re eating. I talk about your relationship with food, how to take back control, and how to master yourself through your food choices. This is not about losing weight, specifically. This is the process to master your diet. Mastering your diet is about your mindset, your attitude toward learning, your willingness to sacrifice immediate results for long-term success, your motivation, and your habits.

3. Do I think I have to “earn my calories” when trying to lose weight?

Dieting makes food your enemy and makes you believe you have to “earn your calories.”

This is wrong.

Meet cravings with real food. If the afternoon lull hits, don’t try to resist, ignore, or “outwill” feelings of hunger. Instead, meet your craving head on and feed yourself with real food. When you change your lifestyle, the first few weeks will be tough. As your blood sugar levels even out, it’s far less important how much you’re eating and far more important what you’re eating. Eat more than enough of the good stuff.

I don’t care if you’re having five real meals per day. You want to feed yourself with MORE than enough of the good stuff to overcome cravings.

I repeat: the ONLY objective for you is to overcome the cravings. I cannot tell you how many times this has helped my clients overcome temptation in the beginning—merely eating healthy food whenever tempted otherwise. (As opposed to trying to ‘push through’ and starve themselves when they’re either hungry or their blood sugar is out of whack and making them feel hungry.

The only thing that matters is that you develop a new relationship with food.

4. If I make a mistake and eat something off plan, do I believe the “day is ruined” and sabotage myself even further?

Often our emotions can sabotage our greater goals because change is hard and our emotions don’t respond well to “hard.” That’s fine. We pay you respect, dear emotions, but you aren’t our king!

Anchoring the day with healthy habits that do and don’t have anything to do with eating will domino and, over time, compound into sweeping change. Once you notice yourself doing things that are healthy for you, that support your health and greater goals, that you imagined yourself wishing you could accomplish—you’ll begin to see yourself from a new perspective, and you’ll feel inspired by seeing yourself change.

5. Do I believe that the only way to succeed is to be absolutely perfect?

My clients have tremendous success when we strategize together how they’re going to get through a particular challenge, such as a business lunch at a restaurant they’re not familiar with, or a board meeting in which lunches are ordered for them—BEFORE THEY GET THERE.

It’s important to note that “Playing to Perfect” won’t serve you here and that “Good Enough” is the way to go. If there isn’t an option that’s 100% on our plan, the strategy is NOT to starve yourself. Be at peace with your imperfect choice, make it as close to our plan as possible, and move on. This is not an opportunity to go entirely off plan, but rather an opportunity to prove that you can live in-between the extremes in the grey.

6. Do I believe that to be successful, I have to restrict my choices to foods I don’t enjoy, or weight-loss plans that allow for little variation?

Diets, generally speaking, are restrictive, absolutist, and quantified. Which means, your relationship with food is one in which you’re constantly measuring against how much you’re not allowed. “That’s not on the plan,” or “I’ve had too much,” or “I’m at my points limit for the day.” The food is shit, the process is torturous, the whole thing incongruous to your actual lifestyle, you’re always hungry, and you’re always thinking about food in an unhealthy way.

And you wonder why your dieting attempts haven’t been successful?

7. Do I believe that eating low-fat/low-calorie is the best (or only) way to lose weight?

My job is to make sure that you never go hungry. We do this by eating enough protein and fat.

“Fat! OMG!” Calm down. Fat doesn’t make you fat.

“But I thought this was a diet!? Doesn’t that mean I need to starve myself and be unhappy?”

This is not a diet. This is a way of life. Life is not meant to be restrictive but to live in harmony. We’re interested in energy, not depletion.

8. Do I come home at night and look to food for relief, either from stress or boredom or loneliness?

For many of us, we have emotional attachments to food—whether or not we know it, whether or not we think of it that way. These are deeply ingrained, and they cause cognitive biases that are VERY hard to detach from.

For example: Do you often feel like eating when you’re bored? How about if you’re stressed, or sad, or lonely? Do you pair food with “relaxation”? Do you often say you work hard, therefore you “deserve” this treat or that outlandish meal,etc. ?

Those are all cognitive biases that you now consider to be “truths.” They’re loosely defined operating principles that condition how you treat certain situations. They’re not inherently ‘bad’ or ‘wrong.’ It’s simply that they’re emotionally-based.

They generate from a place of vulnerability. “I deserve it” means that whatever is in front of you isn’t enough – and therefore you need more. More of what? More fulfillment? So is that what it is? Is the food FULFILLING YOU? Is it honestly expanding your worldview, pushing you to grow in your business, create great art, or helping you to feel more social or be a better lover?

9. When I go “off plan,” can I stop myself from binging… or is it more like permission to binge?

If you’re finding yourself binge-eating, here are 3 quick and highly-actionable tips for the morning after:

1. Throw out the bad food. Throw out any remnants from the previous night’s binge. If there’s bad food around, you will eat it – if not today, then at some other time. Get rid of it. Literally walk it outside your apartment and place it in the trash, outside, in public. Yes, that means you have to get up out of bed and walk outside.

2. Prepare. Take action now to get right back on track for the rest of the day, tomorrow, and the week ahead. Do you need to go grocery shopping? Mobilize and get lunch prepared for tomorrow and, if possible, the rest of the week. Unthaw tomorrow night’s dinner. Take action immediately and train the right behavior. There’s always something you can do to get back on track.

3. Journal. Do some deep work and write about the experience. Putting pen to page is cathartic. You will see yourself from an entirely new perspective when you write it down. Externalize the bad thoughts and tap into your Why. At a practical level, unpack what happened this time and what you can take away to prevent it from happening again. What led to its unfolding? What can you do better next time to mitigate or sidestep the damage while it’s happening?