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How to Make Healthy Habits Stick (Especially If You’re Always Starting Over)

July 7, 2025

Ever look at someone who does it all—eats healthy, exercises regularly, sleeps well—and wonder why you can’t seem to pull it off?

It’s easy to think they have more willpower. Or better genes. Or some secret you don’t.

But more often, the real difference is this: They didn’t get to where they are overnight. 

They built healthy habits slowly—one at a time—over months and years. You just weren’t paying attention while it was happening. 

You’ve probably heard the saying: “It only took me 20 years to become an overnight success.” The same is true for lasting health changes.

So what do you need to make that evolution happen? It starts with learning how to work with your habits—and with yourself.

Here are 4 ways to do just that.

Strategy #1: Shrink the Task 

Let’s say you decide you want to eat six servings of vegetables a day.

But right now, you only eat one or two.

That’s a big change. 

Why? Because it’s going to require you to think about vegetables at almost every meal, shop differently, prep more often, and adjust your tastes and habits.

It’s easy to underestimate how many small decisions that adds up to—and how quickly it can start to feel like too much. That’s when many folks flounder.

When something is too hard, it’s natural to give up altogether. But there’s another option: “Shrink the task.” 

How To Do It

Start by deciding on how many additional servings of vegetables you feel you can consistently eat. 

But before committing, ask yourself, “On a scale of 1–10, with 1 being ‘it sounds impossible’ and 10 being ‘I can do this in my sleep,’ how likely am I to follow through?” 

If your answer isn’t a 9 or 10, make it easier. Then ask the question again, and repeat until you’re at a 9.

You might end up with just one more serving a day to start. Or it could be two extra servings, five days a week. There are no rules, except this one: Shrink the task to a level where you’re very likely to succeed—even if it seems ridiculously easy.

Once you’ve proven to yourself you can do that consistently, choose a new target.  

And if what you thought was a “10” turns out to be harder than expected, no problem—shrink the task again until you’re absolutely nailing it. Success builds on success.

Strategy #2: Think on a continuum

Ever plan on doing a 30-minute workout, but realize you only have 27 minutes, so you skip the whole thing? 

You might say, “If I can’t do my full workout, it’s not worth doing at all!”

This type of all-or-nothing thinking is very common. So common, in fact, there’s a name for it: It’s a “cognitive distortion,” a term popularized by David Burns, MD, a renowned psychiatrist, to describe irrational thought patterns that skew your perceptions, hinder your progress, and mostly make you miserable.

To overcome this, practice thinking on a continuum.

How To Do It

If you can’t do 30 minutes, can you do 25? Or 20? Or 10? Even a shorter workout is better than none and helps build the habit of consistency and keep your momentum going. 

This works with any health habit, and most anything in life, too. 

For example, let’s say you planned to eat healthy all day, but succumbed to free donut day at the office. In that moment, you can fall into all-or-nothing thinking—or you can look for what’s in between “all” and “nothing” (otherwise known as “something”).

Here are a few examples:

Each time you make a choice along the continuum—instead of sticking strictly to a binary option—you’re demonstrating what psychologists call “cognitive flexibility.” And who doesn’t want that?

When you come to a crossroads, think, ‘Am I thinking rigidly or flexibly?’

Strategy #3: See what happens. Then ask, “Why?” 

Often, when people struggle to make a healthy habit change, they blame themselves, saying: “I’m just not strong enough,” or “I don’t have enough willpower.”

But what if you didn’t look at failing as a referendum of your character? What if, instead, you looked at it as a learning moment? Especially if you keep struggling with the same thing over and over?

How To Do It

When a habit slips, pause for a moment and ask yourself: Why did that happen?

You’re not looking to beat yourself up. You’re looking for patterns. 

Maybe you always snack late at night when you’re stressed. Maybe you skip meditation when your morning feels rushed. Maybe you stay up too late when your phone is in the bedroom.

Once you spot the pattern, you can start making small adjustments—ones that address the real reason behind the slip, not just the surface behavior.

That’s how habits actually get stronger: not by gritting through failure and hoping you’ll do better next time—but by learning from it and taking a different approach. 

Strategy #4: Give Yourself Room to Be a Beginner

We just talked about how important it is to learn from your mistakes. But just as important is how you treat yourself before you even begin.

Too often, people expect to be great at a new habit from day one.

But if it’s something you’ve never done consistently before—like learning how to prep healthy meals you’ll actually want to eat, or getting yourself to work out even when you don’t feel like it—why would you think you’re going to be perfect at it from the get-go?

No one expects to run a marathon the first time they go for a jog. You train. You build up. You figure things out as you go.

It’s the same with habits. You’re not supposed to have it all figured out. You’re supposed to be learning.

How To Do It

Pick one habit you want to improve. Then frame it as a skill you’re developing.

Instead of: “I have to do this perfectly.”
Say: “I’m learning how to get better at this.”

This mindset shift makes it much easier to stay consistent—and to stick with it when things don’t go perfectly. You aren’t a failure if you “mess up”; it’s a natural part of the improvement process. 

Remember: Creating health is a lifetime pursuit.

And trial and error is part of the process.

If you’re not where you want to be right now, maybe it’s time to try a different approach—one that’s less about pressure and more about progress.

Use the strategies above, and focus on taking consistent action, even if it feels tiny.

And if you want support along the way, consider joining the Hyman Hive—our private community where we focus on one small health shift each month. You’ll get live events with me and my team, monthly health challenges, and a like-minded group to keep you motivated, accountable, and moving forward.

Start where you are. Do what you can. Then do it again tomorrow. Rinse and repeat.

Because in the end, people tend to overestimate what they can accomplish in the short term—and way underestimate what they can accomplish in the long term.