The Reason You’re Struggling To Form Healthy Habits

If you’ve ever tried to form a new habit or Googled ‘how to build healthy habits’, you’ve probably come across rhetoric similar to:

“It takes 21 days to form a good habit”
“Get a workout buddy to make sure you go to the gym”
“Eat on smaller plates”

And yet, many people are still failing to form healthy habits every year. With all this literature and science on habit formation, shouldn’t we all be able to apply these rules and achieve our goals?

We’re All Different

better than before

According to bestselling author, Gretchen Rubin, in her latest book, Better than Before, she proposes that there is no one-size fits all solution. Immediately, this makes sense.

We all have different personalities, routines, biological make-up and are unique in every way; applying the same rules to everyone is a surefire path to failure.

How then, are you supposed to find the habit formation system that works right for you?

The approach that Gretchen describes, quite frankly, blew my mind. I highly recommend this book for anyone who has struggled with forming healthy habits in the past. It resonated instantly and I found myself mentally putting friends, family and clients into categories based on the habit system that would work for them.

The Four Tendencies

Gretchen sorts people into four categories, or rather, tendencies, based on their response to expectations:

  • Inner expectations (your expectations of yourself)
  • Outer expectations (the expectations people have of you)

The four tendencies are:

  • Upholders: these people respond readily to outer and inner expectations
  • Questioners question all expectations; they’ll meet an expectation if they think it makes sense
  • Rebels resist all expectations, outer and inner alike
  • Obligers meet outer expectations, but struggle to meet expectations they impose on themselves

To figure out which one you are, select the category with the phrases that most sound like you:


  • Craves ‘gold stars’ and praise
  • Meets deadlines
  • Looks forward to crossing off their to-do lists
  • Thrives on execution
  • Doesn’t like making mistakes


  • Questions rules and accepts only if it makes sense
  • Doesn’t like spending time and effort on things they don’t agree with
  • Tendency towards skepticism
  • Won’t accept facts or rules at face value


  • Doesn’t like the idea of a routine
  • Resists control
  • Doesn’t like being told what to do
  • Wants to do the opposite of a rule
  • Motivated by freedom


  • Listens to other people’s rules, not rules they impose on themselves
  • Has difficulty saying ‘no’ to social obligations
  • People pleaser
  • Doesn’t want to let other people down
  • Others come first before themselves

Let’s put this further into context, with an example we’re all familiar with: going to the gym (or the lack thereof). Here’s how the four different tendencies may respond:

  • Upholder: has it scheduled in their calendar and goes on their own, three times per week
  • Questioner: will only do the amount of exercise they feel is necessary for their personal goals, and will choose the most efficient option.
  • Rebel: finds the gym too restrictive and mainstream, will only do what they like, when they feel like it
  • Obliger: has had multiple failed attempts at forming a gym routine and continues to pay monthly fees. They only stick with something if someone is expecting them there i.e. personal trainer, friend

Where Do Most People Fall?

It is likely that one of those categories resonated the most with you out of the others, even if you saw hints of yourself in other categories as well.

Based on Gretchen’s research, she found that most people were obligers and questioners. Interestingly, I found the same with the clients I’ve worked with. Of course, this is skewed sample size, as I don’t expect upholders or rebels to work with me. Rebels would find working with a coach too restrictive, and most upholders wouldn’t need my help.

Obligers work with me because they need the accountability and someone tracking their food and lifestyle habits. And questioners work with me because they are looking for expert opinion and validation.

If You Were Curious…

I would say I’m 90% an upholder, with aspects of the questioner and obliger for certain areas of my life. My life is scheduled into my calendar and I thrive on crossing off daily and weekly to-do lists. I was a straight A student and loved getting stickers, awards, and still thrive off of praise and recognition. Yes, I know I’m extremely lame.

My husband on the other hand, is a questioner and literally – questions everything and gets very philosophical. He thrives on building efficient systems, discovering new ways of thinking, and of course, despises the phrase, ‘because we just have to’ when I try to convince him that sometimes we need to play by certain cultural rules and expectations so that we’re not ousted from society.

Understanding my tendency has helped me get real about my psychology and how my weirdo brain works. For example, if I put ‘the gym’ on a physical (pen and paper) to-do list and it’s not checked off, it will eat away at me.

How To Build Healthy Habits (Like Exercise) According To Your Tendency

Now that you know which tendency you lean towards, here are some tips for implementing a healthier lifestyle based on your type:


  • Use gamification to achieve targets or unlock levels e.g. Muse, Headspace, Fitbit
  • Schedule exercise into your calendar or physical to-do list, post-it note, whatever works


  • Decide what you are and aren’t willing to give up for a healthier life (understand your why and then stick to it). E.g. I am not willing to waste time on a commute for the gym as I hate being rushed for work, so I will work out at home.
  • Again, understand the why behind healthy eating habits instead of accepting guidelines
  • Isolate all of your excuses, and then find a way to shut each one down with an adjustment to your routine


  • Take part in exercise that gives you a sense of freedom e.g. kayaking, rock climbing
  • Get a solid understand of how to eat healthier, and then eat intuitively vs. following any rules
  • If possible, create your own schedule outside the 9-5 for more mental peace


  • Join a group fitness class e.g. CrossFit
  • Hire a personal trainer and/or nutritionist
  • Track your food intake on MyFitnessPal and add friends
  • Make public declarations of your goals so you follow through

I hope this framework has been eye-opening for you, I can’t stop seeing the world in this way now that I’ve been exposed to it. Let me know what you think and if you’re going to try out any of the tips above!


About Alina

I'm a Holistic Nutritionist based in Toronto, Canada and my official title is Certified Nutritional Practitioner (CNP). I received my diploma in Applied Holistic Nutrition from the Institute of Holistic Nutrition. I'm a coach and an educator. Follow Alina on Facebook, Twitter, Pinterest and Instagram for all of the latest updates.
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  1. I am surprised to find that I switch between the different tendencies! So I have learned something new. Your article is very useful, as I now know that I need to figure out where I am at before attempting any program of transformation.

    1. Thanks Celeste! I also think you’d love reading Gretchen’s entire book, ‘Better than Before’. I only just scratched the surface with this article…so many more useful tips in there!

  2. Huh! I use the put it on a list trick and fit the upholder profile – and am commenting so validation much?!

    I can also excel at questioning my original goal if I want wriggle room though – I love your concept of hunting down excuses and designing them out. I’ll be designing in fun too -too much inner expectation without escape and I rebel right out of there – very unobliging when I genuinely want good health! Yes, it is a noisy place in my brain- hence lists ?

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