We've all been there: you start a new habit with the best intentions, ride the wave of initial motivation for a few weeks, and then... life happens. Maybe you miss a day, then two, and before you know it, that promising new routine has quietly slipped away. If this sounds familiar, you're not alone—and more importantly, it's not a character flaw.

The truth is, most habit failures aren't about lacking willpower; they're about missing the troubleshooting skills that turn temporary setbacks into permanent success. Whether you're struggling to get started, constantly falling off track, or finding endless excuses to skip your routine, this guide will help you identify what's really going wrong and give you the tools to fix it for good.

A common stumbling block is getting started or not knowing where to start. Starting a new habit requires an initial burst of energy. The energy requirements of getting started are greater than the energy needed to maintain an established habit. Here’s a few ways to find that initiation energy:

A fresh start increases your motivation to change because it gives you either a real clean slate or at least the impression of one. New Year's Day is the classic example of a fresh start. Last year was the old version of you and this year is the current version that is going to make changes.
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​This is also way you are more likely to start the diet on a Monday. You can create your own fresh start at any time by setting your metrics back to zero.

Look around you right now. No, seriously, right now. Find one thing  - the smallest step - you can do this very second. Have you been struggling with starting an exercise routine? Do one squat. Right now!
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​Great! You've gotten started. You've taken the first step and you can build on that.

For some, starting small isn't motivating enough to take the first step. It's time to go big and start with high-intensity. Sign up for a 30 day challenge, overhaul your kitchen pantry, or turn your basement into an art studio and buy all the supplies. 
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​The key to success with this method is to figure out a way to transition your big change into a sustainable habit you can maintain on a daily basis.

Sometimes a big life change will create a fresh start for you. A significant life event will force you out of establish routines and provide you will the opportunity to create something new. It could be a move, a new job, getting married, or having a baby. These are almost impossible to manufacture, so be aware of when they arise naturally in your life so you can be ready.

One factor affecting your ability to change is not knowing where to start. Maybe you have several things you want to change or you know something needs to be different but you can't pinpoint what it is. Here are some things you can try:

The Miracle Question was developed by Steve de Shazer and Insoo Kim Berg, who are considered the founders of Solution-Focused Brief Therapy. This  question will help you gain clarity on where to get started.
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​It goes like this: A miracle happened overnight that fixed your critical problem. What are the first things you notice, after you wake up, that reveal the miracle happened? You don’t know the miracle took place and when you wake up, you begin to notice things that tell you the miracle has happened.
Don’t focus on the way that you feel but on actual observable behaviors. What’s the first thing you notice? What might others notice?

For example: If you are stuck in an unfulfilling job and you miraculously wake up in a job that is fulfilling and what you want - you might identify the skills and actions needed to make it a reality. This is very similar to manifesting. You’ve identified the outcome and work backward to identify the steps you need to take to get there. Try to get a concrete as possible.

To help you get started, get to the root of what you want to achieve - or the goal of the goal. What is at the core of why you want to change? Ask yourself a series of "why" questions.
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​This is commonly seen with weight loss goals. An arbitrary weight loss goal is set (often by a doctor or by societal standards), but often it is lacking a foundational reason. Take time to ask yourself why you want to reach this goal. Sometimes it stems from a health concern but often it’s tied to a deeper meaning - it’s to have more energy, enjoy time with kids or grandkids, or to feel more confident. Maybe there are better ways to accomplish getting to the root goal achievement?

If all else fails and you have no idea where to start, start with sleep. It’s is a cornerstone habit - meaning if you have your sleep dialed in, other habits will naturally follow. Start working on behaviors that will improve your sleep. Tip: Set a bedtime for yourself. Use an actual alarm. It doesn’t matter what time that is when you are getting started. Make it realistic - even if that’s 1 am - the goal here is to develop consistency with it before you adjust.

Inevitably, things will go wrong. You will encounter obstacles, physical and psychological. When approaching behavior change and habits, the best way to overcome your obstacles is to anticipate and plan for them. Because it's not a matter IF things go wrong, but WHEN things go wrong. 
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​Not everything is foreseeable, but if you've laid a good foundation and done the work of getting to know yourself, you'll have insight into what will trip you able. You'll be better prepared and hopefully, easily hop over those hurdles.
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​Let's explore further:

The foundation of habits and behavior change is built on three things:
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​Values
​Get a clear understanding of what you value in life. Ensure your habits align with your values.
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​Identity
​Identity is at the core of your behavior. Once you decide the type of person you want to be (based on your values), then you prove it to yourself with your habits. Each time you perform the habit, it’s a vote for that identity. Start telling yourself you are this person, even before you feel it.
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​Expectations
​Are you expecting prime rib but only have PB&J energy? You might not even realize you have these expectations. Take time to identify then manage your expectations. Adjust your habits to match your energy.

Get to know yourself - your personality, preferences, idiosyncrasies. The more you know about yourself, the better you can execute your habits. You'll be working with yourself, rather than fighting your natural tendencies. Here are a few key aspects to consider:

How you are motivated
Are you prevention-focused or promotion-focused? Knowing this will help you word your intentions and goals in a way that is motivating to you. Which sounds better? "Quit eating junk food" (prevention) or "Eat better" (promotion). Or "Get more sleep" (promotion) or "Stop staying up so late"(prevention).

Peak energy time 
​Are you a morning person or a night person? When you are faced with starting a new habit, take advantage of the times you have the most energy.
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​Take personality tests
​Personality tests can give you insight into yourself. Here's a couple to try to help with habits and learn how you are motivated: The Four Tendencies and the Enneagram.
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​Journaling
​Getting thoughts out of your head and on to paper can help you process your thoughts and feelings. Afraid of the blank page? Check out this list of 90 journal prompts from Ness Labs.

Habits, especially when the are new, need to be guarded from our normal human tendencies. One way to do this is by setting up safeguards. It's a way to protect your habits and keep a small lapse from becoming a full stop.

Your safeguards will be determined by your habit and your personality. The same thing won't work for every one. Instead of resisting temptation, you anticipate and minimize temptation. In other words, plan for failure. 

James Clear's motto is, "Never miss twice." Adopt this as your own motto. It allows you the opportunity to miss, but a way to get back on track. quickly. Similarly, set up planned exceptions. Maybe you take weekends off from your habit. Or your safeguard is that you have to complete your habit at least four times a week.
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​Safeguard could also center around what you allow in the house, like alcohol or junk food. The great thing about safeguards is that they can be personalized to work for you.

Friction is the mental and physical circumstances that create resistance when it comes to behavior change. Unlike barriers or obstacles which are the big things that stand in your way, friction is the little things - and some you might not even be aware of.

As humans, we gravitate toward the path of least resistance, so if we encounter resistance on our path to our habit, we are less likely to complete it. Friction doesn’t always stop forward movement, but it does slow it down and get in the way of progress because you must put in extra effort to complete the habit.

An example of friction is changing into gym clothes. Sometimes we drag our feet getting changed to workout that we miss the opportunity. Smooth out that friction by changing into your workout gear before you leave work, then head directly to the gym. 

Or if you have a morning sweat sesh, lay your clothes out the night before and change immediately upon waking. Then go get your coffee. You're changed and ready to go as soon as you're caffeinated. You could take it a step further by sleeping in your gym clothes (maybe a bridge too far...).

It sounds simple and a little silly, but that’s the nature of friction. We let the smallest things stand in our way - especially when a habit is new.

Retailers take advantage of friction reduction all the time by making the checkout process as easy as possible. Shopify is by far the best at this - it saves your payment info across retailers. In two clicks your purchase is on the way to your doorstep.

Be the Shopify of your habit by identifying the friction that is standing in your way and work to eliminate it.

We are really good at coming up with "reasons" for why we should be excused from completing our habits. It's not something that we've planned for, but a spur-of-the-moment decision that let's us off the hook. Gretchen Rubin calls these "loopholes." There are several that she's identified:
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​Moral licensing loophole
The basic idea is that when we've done something virtuous or stuck to our good habits for a while, we feel we've earned the right to break those habits.  It makes breaking our habits feel not just justified, but earned. We're not being weak or giving in to temptation - we're rewarding ourselves for being so good! This makes it feel virtuous rather than self-sabotaging.

Unfortunately, good behavior doesn't create a "credit system" where we earn the right to engage in the behaviors we're trying to change. Our habits work best when they're consistent, not when they're treated as a balance sheet of good and bad choices.

Tomorrow loophole
Now doesn’t matter because you will do it tomorrow. Like with starting a diet: I’ll eat garbage today because the diet starts tomorrow. We fool ourselves into thinking that we are different people in the future - like extreme indulgence today will give us better self-control tomorrow.

False choice loophole
This is when we pose that two activities are in opposition, and we have to make an either/or decision, when in reality, they aren’t necessarily in conflict. Example: like putting fun and easy things on your to-do list and saying that you have to do them because they are on the list, leaving no time for the important things.

Arranging to fail loophole
This is when we purposely put ourselves in tempting situations that we find almost impossible to resist. If you know you have trouble with controlling the amount of video games you play - picking up the controller and saying you are only going to play for 15 minutes before you go to the gym - is putting yourself in a situation where you are likely to fail. Or if you are working on cutting down on drinking, having a bottle of wine in the house for guests is eventually going to be too much temptation to resist.

“This doesn’t count” loophole
We have a thousand reasons we tell ourselves that for some reason, this circumstance doesn’t count. Like when we're on vacation, the holidays, on weekends, extra stress, or a heavy workload. But, with habits, it all counts.

Concern for others loophole
You find yourself in this loophole when we tell ourselves that we’re acting out of consideration for others and making generous, unselfish decisions. Or we decide we must do something in order to fit into a social situation. It could be not wanting to seem rude by passing on a piece of cake. Or not asking your partner to stay with the kids to get in a workout. Or not wanting to seem "holier-than-thou."

Fake self-actualization loophole
This loophole works by using grand language about living life to the fullest or being spontaneous to justify breaking a habit or making a decision that goes against our long-term goals. For example:

Splurging on expensive clothes because "life is short and I deserve nice things"
Skipping a workout because "I should be spontaneous and flexible"
Breaking a spending habit because "you have to seize opportunities when they come"
Abandoning a healthy eating plan because "I need to enjoy life's pleasures"

The fake self-actualization loophole is particularly sneaky because it disguises impulse decisions or habit-breaking as profound, life-affirming choices. It makes breaking good habits sound noble and enlightened rather than what it often is - a momentary lack of self-control dressed up in fancy language.

“One-coin” loophole
This loophole comes from the argument of the growing heap. One coin doesn’t make you rich, so how much could one coin matter? But you only get rich by accumulating coins - one coin at a time.

In the context of loopholes, it’s when you excuse yourself of doing it by saying, “What does the one time matter?” When you resist this loophole and you add the coin, the pile of coins grows bigger, the habit continues, and it protects the habit, making it stronger.

By making yourself aware of these loopholes and paying attention to the things you say to yourself, you are more likely to avoid these pitfalls and keep your habits strong.

During this show segment, we introduce four ways to interact with the material presented: A question to answer, a quest to complete, an aspect of creativity we've noticed this week, and a quote to ponder.

What is the biggest barrier for you when it comes to establishing or breaking a habit?

Reflect on your habits and identify areas to troubleshoot and improve.

A quick and creative way to hang curtains: Kwik Hang Curtains

"Creativity is a habit, and the best creativity is the result of good work habits."
​- Twyla Tharp

Episode 42: Goal Setting & Habits
Episode 11: Reducing Friction
Episode 37: Developing the Habit of Creativity
90 Journaling Prompts for Self-Discovery from Ness Labs
​The Four Tendencies Quiz by Gretchen Rubin