This is Why You Struggle to Maintain Your Good Habits

Do you have a habit that you really want to keep, but for one reason or another, you can’t make it stick?

Is there a goal that you’re working toward but, because you’re worried about failing or what other people might think, you hold back from going all-in?

Have you wanted to make a change in your life for a long time but you find yourself unable to move forward?

If so, you might be “stuck in the maybe.” And I have some strategies you just might want to try.

In episode 62 of the I’m Busy Being Awesome podcast, I explain exactly what it means to be “stuck in the maybe.” 

We talk about how it might be holding you back from leveling up in your life.

And we explore what you can do to step out of “maybe” and into commitment as you work toward that new habit or big goal.

You can listen to the episode below, or stream it on your favorite podcasting app here:

Prefer to read? No problem! Keep scrolling for the entire podcast transcript.

Listen To The Podcast Here!

In This Episode, You Will Discover… 

  • Exactly what it means to be “stuck in the maybe”
  • How this might be holding you back from leveling up your life.
  • Four powerful strategies to help you step out of “maybe” and into commitment as you adopt your new habit or reach the next goal.

Links From The Podcast

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Episode 62: This is Why You Struggle to Maintain Your Good Habits

Hey, everybody! Welcome to the podcast. What’s going on with you?

Before we dive into today’s topic, which is all about getting stuck in maybe, I wanted to share something that’s coming up in October. 

Self-Coaching Webinar

Over the last few weeks, I have heard from a handful of different folks asking me about my thought work and morning journaling practice. Of course, I talk all the time about how powerful thought work is, and the value of getting your thoughts down on paper on a daily basis. I really do believe that it is the core secret to reaching any goal in your life. And it sounds like many of you would like a little bit more guidance on how to actually put this into practice.

So first of all, I am planning a podcast on journaling specifically within the next few weeks here, so stay tuned for that. But I also decided to teach a webinar/workshop on my exact process to identifying the problems and creating solutions to any problem in your life with thought work, which is exactly what I do with my thought work process each morning.

That way, after the webinar, you will have your marching orders. You’ll have an easy, step by step approach to exploring your own thoughts, and beginning your own self-coaching practice.

Sign up!

Now, this will happen in October. And if you want to get your name on the list and be notified about the details of the webinar, when it will take place, the Zoom link, etc. Just head to You can add your name to the list, and I will send you an email with a heads-up with all of those details. So again, just head to

What Does Getting Stuck In the Maybe Mean?

All right. What are we talking about today? Well, today we are talking about a concept that I’ve termed, “getting stuck in the Maybe.” Now, this is not an official term. This is something I made up. But I think it does a good job of detailing this situation and the mindset that I want to talk about in this episode.

So. Getting stuck in the maybe. What am I talking about? What does this concept mean? On the grand scale, getting stuck in the Maybe is essentially a form of indecision. But the way that I have been hearing it in my clients, and in myself, and from my friends, has a slightly different flavor than that.

When I think about getting stuck in indecision, it usually means not knowing what to do. That usually sounds like should I buy this thing or this thing? Should I say yes or no to this offer? Should I agree to participate in this committee or not? That’s the kind of thing I think about in terms of working through indecision.


Getting stuck in the maybe, however, is a little bit more nuanced. I think it’s a little sneakier. And the big difference is that it has more to do with establishing habits or following through on a plan, or being consistent, rather than making a one-time decision of whether or not you will do something.

So that’s what we are doing today. We are talking about what it means to be “stuck in the maybe” so that we can start identifying where it might be happening in our life. We will talk about how it could be holding us back from reaching the next level in our goals. And we’ll talk strategy about what we can do to step out of it and move forward so we can create those habits, follow through on our plans, go all-in on the things that matter to us, and establish greater consistency in our lives.

Where We Get Stuck

Now like I said. I have noticed this popping up in several different situations recently. I’ve seen it in myself. My clients are working through it. And I’ve noticed it in some of my friends as well.

So, what does it actually look like? How do we know if we’re getting stuck in the Maybe? I’ll give a couple of general examples, and then I’ll pull from some of my experiences to help highlight it a little further and put things into perspective.

Habits: Going All-In

So, one of the biggest areas where I see people “getting stuck in the maybe” unfolds is in terms of not going all-in on something you want to do. And this is for both small habits and big goals and dreams.

Waking Up Early

So for example, maybe you really want to get up earlier to work on your writing in the morning. And you keep telling yourself you “should be doing that.” And you “really need to get up earlier.”  But for whatever reason, it’s not happening. You haven’t fully committed to the new habit, and instead, you just keep going back and forth telling yourself you should, and then not actually committing to the plan. And you’re stuck in the maybe.

Using a Planner

Or maybe you want to start using your planner regularly. You really want to map out your day ahead of time, and you are so excited to adopt that practice. You completely believe in the benefits, and you know your day would be so much more efficient if you planned it out. But then the days keep slipping by, and you don’t make time to plan. You find a reason not to follow through. 

Establish a Writing Habit

Maybe you really badly want to start your new business or write a book. You can see the potential. You can see the opportunity that awaits you. And you know the value you have to offer. But you’re stuck in the maybe because you’re doubting yourself. You don’t know if you really have what it takes. You spin out worrying about what others will think of you or what might happen if the business fails. So you dabble in the idea without ever going all-in

This, my friends, is getting stuck in the Maybe. You’re stuck in the back and forth knowing you want to do something but not following through on it. Whether that’s because you think you can’t, or you don’t believe in your ability to see it all the way through, or you’re afraid of failure, or the million other thoughts and reasons that might be holding you back from your particular situation.

Getting Enough Sleep

And believe me. I get it, I KNOW how it feels. I know the feelings of fear and uncertainty that come up when you don’t know if you really have what it takes. So instead of going all in, you just tiptoe around the edges of possibility. I know how frustrating it can be when you think you can’t stick with anything no matter how hard you try. So you might try something a few times, but you’re not surprised when it doesn’t become the habit you truly want to establish.

In fact, I started playing around with this concept of “getting stuck in the maybe” a little over 4 weeks ago when I was not going all-in on a habit that had I wanted to establish for YEARS.

And the area where I was not going “all-in” was going to bed on time so I could get the sleep I needed. I am not kidding when I say I was a broken record for close to 10 years. I’m a little embarrassed to admit it. But for years and years I was consistently telling myself and my poor husband, Ryan, that “I really need to get to bed early tonight. I need to get more sleep. Arg, I just can’t seem to get to bed on time.” Seriously, I was annoying myself. Because I was constantly telling myself I would do one thing, and then I’d find some reason or excuse not to follow through and I’d stay up late.

I knew the value of sleep. I knew how much better I felt when I got it. And I knew that getting enough sleep helped with my ADHD and focus levels as well. This was important to me. Or at least that’s what I was telling myself.

Being Honest With Yourself

But the reality was that it was not a priority for me. The reality is that I was prioritizing other things. I prioritized answering emails, doing work, or going on social media. In fact, I thought I had finally figured out the secret by going upstairs and reading before bed, but then I would just read for hours and still not get to sleep on time.

I was totally stuck in the maybe. I was going back and forth, not ready to commit to the new habit. And I was not ready to commit to this decision.

The Shift

So what happened? How did I get out of the Maybe? A little over a month ago I was talking with a friend of mine about my reluctance to go to bed. I was telling her I knew I wanted to, but no matter what I try and I couldn’t make it happen. And as I talked it through with her, I found a new thought that was the missing link. I found the thought that finally had me feeling committed to following through on going to bed on time. And it’s a thought that surprised me a little bit.

I figured in order to make myself get to bed I would have to think of my future self. I figured I’d have to imagine how much more focused and productive I would be the next morning. But again, that wasn’t working for me.

A Challenge

What did work was when I started thinking of it as a challenge or a game. I decided to think to myself, for the next 30 days, you are going to be up in bed with the lights turned off by 10 p.m. No matter what. Let’s see if I can do it! What if I take the challenge for just 30 days? And if I decide I don’t feel better after that, then I can go back to my old routine. But I can do so knowing I gave it an honest try.

So that was my challenge. 30 days, Lights Out by 10.

When I told myself to take the 30-day challenge, it was quantifiable. I could track my progress. And in fact, I even found myself trying to beat my time getting to bed earlier and earlier. And what’s more, because I couldn’t keep reading late into the night as I had been, I found myself wanting to go up earlier so I could get more of my book read.

Now, I’ve finished the 30-day challenge, but it was only about 2 weeks in of sticking to that consistency that I knew I was not going back. I had so much more energy. I felt so much better when my alarm goes off at 5. And I have a much more enjoyable start to my day. Plus, I wasn’t constantly nagging myself – stuck in the maybe – about whether I will or will not follow through on my plan to go to bed early.

Instead, I stepped out of the maybe. I made a hard-and-fast decision that – no matter what – lights out by 10.  It’s non-negotiable. I stepped out of maybe and into committed.


I also see a version of this happen with a lot of my clients when we begin working together. They are “all in” on the coaching sessions. They are all-in on meeting with me each week. But when it comes to doing the daily thought work or the different worksheets or questions I give them to consider throughout the week before our next session, that’s when they get stuck in the Maybe. That’s when they tell me on the next call, “the week flew by too fast. I was just too busy. I completely forgot about it.”

And here’s the deal, I absolutely get it. I know that their days are packed. I know that they have super busy lives. And I understand how easy it is to put self-coaching on the back burner because we have other fires to put out.

In fact, I get it because I used to tell myself the same thing, too. I’d even tell my coach, “You know, I get so much value from our sessions that they carry me through to the next week. I don’t even need to do the thought work each morning.” And I genuinely believed that.

Self Coaching and Thought Work is the Answer

But here’s the truth. And this is why I am SO adamant about adopting this thought work process. Once I intentionally decided and committed to step out of the Maybe and stick to my daily self-coaching practice, that is when everything shifted. Doing this not only completely accelerated the specific goals I was working toward with my coach, but I had huge breakthroughs in so many other areas of my life, too.

Because once you start recognizing and truly internalizing the fact that your thoughts create your results. And once you start intentionally choosing the thoughts you want to think, on purpose, that is when your life completely transforms. That is the secret to the universe.

And remember, I didn’t always feel this way. I really battled with creating that consistency at first. I had the on-again-off-again relationship with journaling for many years, and it took work to establish that consistency. But once I did, it was everything. And like I said, we’ll talk about some of the strategies I use to help me get out of the maybe at the end. 

Open to New Ideas

Now, another area where I see people getting “stuck in the maybe” usually concerns a person’s willingness to try new things and be open to different possibilities. 

Generally, I see this pop up when we hear about something that we — intellectually — believe could be a useful thing in our life. We’ve heard other people talk about the benefits. We’ve maybe even seen its positive impact on someone else. But we’re not entirely sold on doing it ourselves.

So perhaps you recognize the importance of strength training intellectually. You know it’s important to lift weight not only for your current self in terms of your energy and strength but also for your long term health. But because you haven’t really experienced the benefits for yourself in the long term, plus it takes way more work than sitting on the couch, you’re not totally sold. Even though you know it’s good for your future self.

Or maybe it’s keeping a morning or evening routine. You’ve heard about the benefits of creating some consistency or routine to start and end your day. You know lots of people who have told you about the positive impact that maintaining a morning routine had on their life. But when it comes to getting up earlier in order to fit that in, you’re not entirely sold.

Do you have any areas like this in your life?


For me, this was embracing the practice of meditation and stillness. 

Here’s the deal, I have had an on-again-off-again relationship with meditation. I have been stuck in the maybe with this one for years as well. I would begin a new streak of meditation practice for a couple of weeks, and then I would slip back. And I would let it go.

And even though I’d read studies showing the benefits of meditation generally, and I knew about its unique benefits for people with ADHD specifically, I could never seem to stick with it for the long term. 

Then about a week ago I was talking with another coach friend of mine, David, who is – conveniently enough – a contentment coach. He works with people who want to slow down and find contentment in their life. And he’s been telling me for months that I need to spend some time each day just doing nothing. I need to spend some time in the stillness with quiet reflection.

And because I am almost always doing something – I actually felt confused when he told me to practice stillness. My brain thought “I don’t even know what that means.” I’m pretty sure I even asked him, “so what do you mean do nothing? Can you actually explain what I’d do here? Am I meditating? Am I thinking about something in particular?”  He’s like, “No. Just sit and do nothing!”

Doing Nothing

Folks, this was mind-blowing to me.

So David recommended that I check out Ryan Holiday’s book, Stillness is the Key, which is – indeed – pretty fantastic. I will link to it in the show notes along with a link to David’s website if you want to check out his work. And in addition to reading Holiday’s book, David also suggested that I sit and do nothing for 10 to 15 minutes each day.

And again, this is one of those situations where – I knew it would be good for me to do. But for whatever reason, I wasn’t entirely willing to do it. For me, sitting still for 15 minutes a day doing nothing seemed like a total waste of time.

Open to Possibility

But as I opened up to the possibility, and I listened to what David was saying, and I began listening to the words of Ryan Holiday in his book, it started resonating with me more deeply. And I started thinking, you know what? I’m ready. I want to do this. I’m ready to step out of the Maybe.

Now, as I had learned from getting out of the maybe with my sleep schedule, I knew I couldn’t just “try” to make this a habit. I knew I couldn’t just “give it a go.” I needed to do something different.

So instead, I decided to issue myself another challenge. Similar to my bedtime routine, I decided to do a 30-day challenge. Unlike my sleep routine, I haven’t been doing it for very long. As of this recording, I’ve been doing it for 4 days.

We’re All Figuring it Out

And in fact, I hesitated to even share this example on the podcast with you today. Because I often like to share tools and strategies after I’ve worked out the kinks. I want to come to you with a strategy that works for both me and my clients so that you can implement it with confidence as well. 

Of course, in this situation, I don’t have all the answers yet. I haven’t yet figured out how to be consistent with stillness yet. As I said, I’m only four days In.

BUT, I decided to share it with you anyway. First, as a reminder that we’re all still figuring things out, right? We are all continually learning, and growing, and stepping up to the next level. And right now, my next level is learning to allow time for rest – in terms of my sleep – and time for stillness in my mind.

And I’m also mentioning it as a form of accountability. So if you’re listening to this a few weeks or months or – heck – even years after this podcast comes out, check in! Hold me accountable. I’d love to hear from you. 

But for now, I am four days in the 30-day challenge. I’ve stepped out of the maybe, and I am all-in and fully committed. In fact, I have even created a fun habit tracker for both my sleep and Stillness so I can give myself that gold star each time I follow through and have that tiny win. Because frankly, I don’t think we do that enough for ourselves. And for me personally, it’s one more little dopamine hit to help me reinforce the habit.

Start Paying Attention

So I encourage you to start paying attention. Do you hear yourself in a situation like this? Do you hear yourself saying, “I just don’t have time for it”? “I know I want to do it, but for whatever reason, I can’t make it work.” “I know I should, and I really want to, but it’s not happening.”

If you have an area like this in your life. If you have something you want to do, but no matter what you try it doesn’t seem to stick, it’s possible you’re stuck in the Maybe. 

How to Get Unstuck and Out of Maybe

So, let’s talk about what we can do about it.

I have four different suggestions of approaches for you to try in order to help you step out of the maybe and into committed action. And the first has to do with getting curious and exploring whether you like your reasons in a couple of different areas.

Do you Like Your Reasons?

First of all, I encourage you to really question whether you like your reasons for trying to adopt this new habit? Or do this new thing. Or pursue a certain project or goal? Why is it that you want to do this?

Is it that you’re super excited because you can see how it would really improve your life? Or are you doing it because you think you should, or somebody told you you had to, so you’re grudgingly agreeing to do it? Those are two very different mindsets, which are going to produce two very different results. So first of all, get curious about whether you like your reasons for trying to adopt this new habit or do the new thing.

On the other side of the coin, ask yourself do I like my reasons for why I am not sticking to it? If you are trying to write every morning before your kids get up, and there have been several mornings where it just wasn’t working for you because you were up for several hours in the middle of the night with one of those kids, perhaps you like your reason for sleeping in as much as possible instead of getting up and writing during that time.

But if you’re like me and my bedtime battle, I did not like my reasons for why I was staying up. Because my reasons were that I was on social media, or I felt like I needed to answer emails or keep working. And seeing as I had been up since 5 getting things done, there was no reason that I needed to think I should keep working. That was ridiculous. That was a thought error. And I realized I did not like my reasons. So take some time to make sure that you like your reasons in both of these areas.

Equal Airtime

The second area I encourage you to explore is to make sure you are giving equal air time to both the positive and negative situations. So let me explain what I mean here. 

Often when we find we are struggling to stick with something, or we are having a hard time maintaining a new habit. Or maybe you’re stuck in a bigger “Maybe” of “should I do this program” or “should I take this job” or “should I decide to pursue this goal or that project”?

Often when we are stuck in the maybe, we are focusing only on the negative. We are thinking about how we have never been able to stick to this habit before. 

We Often Focus Solely On the Negative

So, “I’ve never been able to maintain writing habit in the past.” Or for me, “I’ve never been able to stick to my meditation.” Or “I’ve never been able to stick to going to bed on a regular schedule.” We think about all of the disasters of “what if it doesn’t work?” And this is especially true when we’re thinking about the bigger “Maybe.”

In other words, if I try this, and it doesn’t work out… Then the world is going to end. All of these horrible things are going to happen. It’s so much better for me to stay safe and not try. And what I invite you to do is give equal air time to both the positive and the negative. So if you are constantly telling yourself that you can never stick to anything, I invite you to challenge at. Where do you stick with things? Where have you built up a habit?

Because when you can find evidence for it, then you can learn from it. You show your brain that you can indeed follow through. We just need to figure out a way to transfer those same skills to the new habit you’re establishing.

Find the Possibility

Similarly, if you are stuck in the catastrophizing a bigger goal or making a choice to take the job or do the program, make sure you’re giving yourself equal air time on how amazing it could be as well. 

If your worst-case scenario is that you are going to try something and fail at it and feel super embarrassed because you told everybody that you know and love that you were going to go after the goal. Make sure you give equal airtime to how amazing it will be when you do reach the goal. The way you will feel when you do make it happen and you get to celebrate with everyone you know and love.

Give equal air time. Because our brain is going to immediately and solely focused on the negative if we let it. That’s what our brain does. It’s just trying to protect us. But we want to challenge that. We want to give equal air time.

Create a Challenge

My next strategy is the one that I have talked about a couple of times so far in the episode, and this is to make it a challenge. Challenge yourself to give it to try for x amount of days, whether that’s I’m going to do it for 14 days, or 30 days. Give yourself an end date to see how it goes. Tell yourself you’re going to stick to it no matter what for that time period. After the time’s up, then you can reassess. Then you can decide whether or not you want to continue moving forward. 

I generally like to stick with 30 days because 30 days is usually enough time to get through the uncomfortable middle period. It’s that period where you’ve lost the exciting shiny-new motivation but you haven’t established the habit yet. And usually, by the end of the 30 days, you have gathered enough data to know whether or not this new habit is benefiting you or not. 

Act As If

And the last strategy that I cannot stress enough is to mentally become the person who does the habit you’re trying to establish.

So what do I mean here?

I mean that we are leaving behind the story and the belief about ourselves that we are trying to become the person who goes to bed on time. We are leaving behind the person who is trying to make time for meditation or self-coaching or working on their side Hustle.

Instead, we are that person.

So we are no longer entertaining the idea that we’re trying to figure it out. No. I am a person who goes to bed before ten. No matter what. I am a person who gets up and writes for 30 minutes every morning at 6 a.m. No matter what. I am a person who meditates or practices stillness for 10 minutes a day no matter what. Become that person.

Don’t let your brain start thinking things like, but what about that one time when we stayed up later than we planned? Or what about that time when we decided to watch the movie instead of going for a run? What about that time or that other time?

Remember this

One of the most powerful things that I have really internalized over the last six months or so is:

You get to decide the story you tell yourself about yourself. 

If you focus on the story that you can never follow through and never stick to anything, that is the story you are going to live out. But if you focus on the story that you always show up. You always follow through on the habit. You always make time for this thing or that thing, that is the story you’re going to live out.

Over the 30 days that I took the 10 p.m. Lights Out Challenge, there were a couple of days when I was still awake past the 10 p.m. cut off. But I didn’t focus on that. I didn’t tell him myself, “oh man, I messed it up.” “I fell off the wagon…”

There is No Wagon

If you’ve been listening to this podcast for a while, you know how I feel about the wagon. There is no wagon. instead, I thought, “Interesting. I made the choice to stay up later tonight. That’s so weird because I always go to bed by 10. What was going on that made me act differently? Why was it that I decided not to stick to this plan today?”

And then I get curious. I find the thought error. And I can adjust.

Or alternatively, there might be a reason that I like. Maybe I was having a Zoom night with my girlfriends one night, and I stayed up later than 10 because I wanted to. I knew I was going past my 10 pm deadline, and I liked my reason for it.

I’m not going to make that mean that I’m not sticking to this new habit. Because I am a person who goes to bed by 10 p.m. No matter what. 

So if you often find yourself thinking different versions of, “I fell off the wagon again.” Or “I slipped up again.” Or “I can never make it work.” I encourage you to leave that story behind. I promise you it is not useful. I promise it is not serving you.

Like I said before, you get to decide the story that you tell yourself about yourself. And I can tell you from personal experience that when you tell the story of how you want to show up, you’re going to follow through with that story and become that person much more quickly.

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