Making Change (& Continuing On When You've Let Yourself Down)

24.02.21 09:27 PM By Heather Kleinschmidt

I used to think that New Year resolution-setting was the dumbest thing. It didn't make sense to me.

It seemed like if you wanted to set an ambition for yourself, there was no reason to wait for a particular day on the calendar to do it. There's nothing magical about January 1.

Now, I appreciate the ritual more than I used to.

It's easy for life to be swept away with the day-in and day-out of endless small problems. And by setting aside January 1, we've created for ourselves a cultural reminder to individually pause and assess where we are compared to where we want to be, and to call ourselves forward into something new.

It's no secret, however, that for many adults, resolution-setting doesn't lead to anything. No change, no transformation. And 364 days later, they're standing in the exact same place.

Creating change is hard.

With the best of intentions, and even the best-laid plans, a desired change (or ambition) can still slip from our hands — and feel further away than ever.

It can seem like what you want is beyond reach and that you're better off abandoning the whole pursuit.

But let's review that idea for a second...

When my laptop screen goes dark, what happens?

I don't immediately send it to the curb and buy a new one. No — I begin checking the components one-by-one.... Did the battery die? Did I overload the RAM and crash it? Do I have a virus?

Complex things sometimes fail. That doesn't mean the whole thing is broken and needs to be thrown out the window; it simply means that there's some component that's broken and needs to be addressed.

It's the same with your ambitions and endeavors... life is complex, you are complex, your world is complex, and change is complex. But so often, when people attempt a change but don't see the outcomes they expected or wanted, they determine it's impossible for them because [insert reason here: circumstance, genetics, upbringing/training, family history, etc] — and throw the entire thing away.

But that dismissal is premature. Like with the laptop, this is just where you need to go through item by item to find the right sticking point, make an adjustment — and see if that takes care of it, or if the problem is somewhere else. It's a finite list, and it's common enough to all humanity — and chances are your answer is somewhere within the confines of that list. (Although it may take a series of tries before you find the right one and apply it in the right place.)

One last qualifier:

You don't need to become anyone you don't want to become. Everything below only applies to changes that you want to make.


For all those moments of "this time, I will follow through"... For all the SMART goals set, the minimalist habits defined, and the routines designed and attempted... and flopped...

You. are. not. hopeless.

It's just time to pull out the troubleshooting guide, dust off, and try again.


Quick Context #1: What Is It About Change That's Hard?

Transitions aren't the same as routine.

There's no momentum. There's no familiarity. There's no practicedness.

And because the new thing is unfamiliar, there will be surprise, and there must be adaptability.

The early stages also require more energy than the later stages. Natural energy comes after you've found some routines and heuristics that allow you to automate behavior, creating momentum... but in the beginning, that's not there yet.

Furthermore, your attempts to create that energy will often be foiled (in the beginning) because...

Quick Context #2: Not All "New" Is Created Equal

Let's look at two types of new:

  1. very new
  2. translatable new (i.e. when you have some previous experience or understanding that translates to your targeted vision of the future)

The more unfamiliar something is, (1) the more intense your emotions will be when attempting to engage with it, and (2) the more mistakes you'll make in relation to it, especially in the earliest days.

Further, you're likely to underestimate your own lack of awareness in relation to your new ambition. Researchers creatively refer to this as "attentional blindness blindness..."

When something is "translatable new," you'll move through the following components more quickly. When it's very new, however, you may move through more slowly.

When something is very new, you'll also be more surprised by just how new and unexpected it really is (thank you, Blindness Blindness). Then, because you've overestimated your own ability to manage it, it can feel particularly discouraging as you hit wall after wall, seeming like you're making no progress at all. In hindsight, it makes sense that you were so dense about it as you went through it — but in the middle of it, it feels incredibly discouraging.


Because transitions don't have the momentum that routine has, and because they involve so many surprise brick walls, they require a different sort of persistence than routine requires.

Transitions require a different sort of persistence than routine requires.

It's the persistence of taking that first step, over and over. Of returning to the foundation, and trying from there, again.

I recently re-watched the Harry Potter films and noticed something...

Time and time again, when facing something new, Harry had to sit back down and learn to master some basic spell in order to face the larger challenge ahead. The film always fast-forwards through those experiences (because they're boring) and focuses instead on the big moments. But the answer to the big moments is always found in the persistence through those small, foundational things — despite the frustration, repeat failures, and tediousness.

As you persist in that, slowly and bit by bit, you'll see tiny streams of light breaking through.

And then you've got it.


As you sort through the frustration though, the tactics below may help.

Looking Under The Hood

When troubleshooting a failed attempt to pursue something new, the following list can be a good starting point.

1. Allow What's Old To Pass

To successfully step into whatever's in front of you, you have to first release whatever's behind you (whether it was good or bad). It's important to give this step the space that it needs so you don't inadvertently drag unnecessary baggage forward with you.

👉  Try this: State what you're leaving behind. And literally say goodbye to it. Write a letter to it or write it a eulogy; maybe design it a tombstone.

More on this:

2. Define The New

Whatever your new thing is, it's important to specify it. Otherwise, it remains a cloudy, scattered mist — and therefore can't become real.

This isn't to say that you'll have all the answers at the beginning. Unfortunately, you'll actually have very few answers, and the things that you do think you know will probably be wrong or shift along the way (remember Blindness Blindness?)

That's ok.

Even if the frontier ahead is vast and wide-open, there's something specific about it that's calling to you.

Whatever you can specify, do. Write it down. Put words on it.

Try out more words and more words and more words. Eventually, you'll get to the right words.

This gives you a tangible, real thing to aim for.

👉  Try this: I call it a "brain dump" or "processing." It's basically unfiltered journaling.

Take a piece of paper (digital or real), and write. Write anything and everything. Write "ummmm... I don't know what to write" when you don't know what to write. Don't worry about clarity, grammar, structure, etc. Let whatever comes come, and write it all down automatically and without trying to manage it.

Create a new brain dump every day or as often as fits your personality. Give yourself a time parameter (e.g. unfiltered writing for 4 minutes) to prevent it from becoming anxiety-inducing. Keep it in one dedicated place so you don't have to think about where to store or find it. (More on this in the next section.)

3. Hear Out Your Inner Conflict

You're bound to have a variety of personalities within you that all have divergent opinions about the place you're currently in.

Each voice inside advocates for its own priority — security, excitement, social standing, etc. — and isn't about to let you just ignore it.

But while each of those voices won't be ignored, they can accept an intentional "no" for an answer. What they care about most is that you don't totally forget about them.

You can say to them...

I can't pursue all of it right now, so between all these options, I'm picking this one because it's most important to me. I'll make sure not to drop below survival level in any other fundamental area. And I'll get to each of these other desires when I can — when this one has been reached, I'll pick a new one to focus on — but for now, it's this one thing only.

But first, you have to hear and to give attention to them.

My favorite way to do this is (again) with a big ol' brain dump.

👉  Try this: As you write, think about everything that has to do with this new place you're stepping into. Begin to let each of those internal voices speak, to have their say. Again: don't judge, don't filter, and don't manage what they say. Let them speak and be heard, and write down what they have to say, no matter how hard it is to hear or to deal with. You don't need an answer yet, you just need to allow each voice to say what it wants to say to you.

Your page may turn into a dialogue between your own inner personalities, as one voice presents an idea, and then another voice responds with its perspective, and they duel back and forth for a little while.

You may need to repeat this a few times, especially if it's uncomfortable at the start.

Again, it's ok to leave it open-ended for a time. You don't need to have a conclusive decision at the end of every writing session. The conclusion will come soon enough when you've allowed yourself to hear everything inside.

4. Identify How, When, & If-Then

We love to dream, but how exactly are you going to take your steps forward?

You've thought about what it might look like to inhabit this change you envision — but when exactly are you going to do this one small part of it?

And if something unexpected falls in your path and you can't take the actions you planned to take, what then? How will you meet the interruption? What will you do instead (and when)?

This is a make-or-break step, and it doesn't need to be overthought.

James Clear describes a study in which researchers found that for 55% of participants, this step was the difference between whether they stuck to a new exercise habit or not.

👉  Try this: Fill in the blanks of the following sentence. (It's best to write it down somewhere rather than just to read/think it.)

"This [month/week], I will [action] until [parameter] on [day] at [time]."


  • This week, I will do a YouTube workout for 20 minutes on Wednesdays at 5:45pm.
  • This week, I will write until I've reached 250 words every day at 10am.

Then, take it one step further and fill in the blanks of this sentence:

"If something comes up and I don't do it at this time, then I'll do it on [backup day] at [backup time].


  • If I have a scheduling conflict and can't do my workout on any particular Wednesday, then I'll do it Saturday at 8:30am.
  • If I have a scheduling conflict and can't write at 10am on a given day, then I'll write at 6:30pm for that day.

Make your vision concrete. Identify very specifically how and when you're going to follow through, and what happens if-then. Then write it down, put it in your calendar, and do each step you've prepared when it comes time to do them (with the following tip in mind...).

5. Build In Margin

The very fact that what you're doing is new means that you can't completely prepare for it. You will inevitably be surprised by things along the way.

You'll be surprised by unexpected necessities. By the requirement of more effort than you thought would be needed on a particular step. By surprising (internal) emotional friction at particular points on the road forward.

The answer to these things is to pre-build in margin.

Margin is the un-allocated space you give yourself for those unexpected things — delays, friction, and important (or unimportant) distractions.

You need margin in the time you allot, in your financial preparation, in your expectations for results, and in the harshness of your self-judgments. Margin for error; margin for surprise. Margin for your own humanity.

Margin, partly, is a form of if-then in your planning. ("If I don't complete everything I intended on x date, then I'll work to complete it on y date.") It's the extra space that you give yourself to make up for shortcomings and for the unexpected.

When you build in margin in advance as a cushion around your plans, you're less likely to become overwhelmed by the reality of what's involved as you actually start to engage with it. There's less of a squeeze, because you've created space for the squeeze.

👉  Try this: After you've created your plans — after you've determined what steps you think you need to take, after you've decided how long you think it will take you, after you've decided on what personal resources you think you'll need to invest...

Add ~20%.

For example, if you think something will take you 5 days to complete at 4 hours/day, and you've scheduled that time on your calendar over a 5-day period, add a sixth 4-hour day to your plans (and label it "margin"). If you finish your project in five days as expected, great. That means you correctly estimated what it would take, which is usually a good sign. But often, you'll underestimate what it takes (which isn't necessarily a bad sign — it's just normal). In that case, when you're mid-way through the five days and begin to sweat as you realize how much you've underestimated what this endeavor would really take, you can look at your calendar and reassign that "margin" time to this project, giving yourself a fighting chance at still completing it within the "planned" timeframe.

6. Apply Patient Persistence

All transitions require patient persistence.

There's always a journey.

Looking ahead at the unknown space in front of you, your knowledge of that space is (and can only be) abstract. As you actually move forward and take action and begin to interact in that space, things get real. As things get real, your understanding of the space is updated. As your understanding is updated, you develop a different relationship to the space than the one you had when it was only an abstract idea.

In other words:

As you practice your 'How, When, & If-Then,' you'll make discoveries. Those discoveries will lead you to adjust your plans. That's good. Use discernment about making those adjustments to your process, and create new strategies. Don't take yourself back to Square One... but do keep your eyes open, learn, and allow yourself to be sharpened.

Keep moving, keep interacting, and stay patient.


Closing Thoughts

New things always take more than we expect them to.

The easier you expect it to be, the more you'll be surprised by the actual path you end up following.

If you've tried and tried to implement something new — or if circumstance has foisted something new upon you — and your attempts to meet the new just aren't working... it can be helpful to slow down and to walk through the above process. To give the transition its due. To recognize that you're not a failure for struggling with this — you're completely normal. But there is a way to walk forward successfully into change.

Your favorite athlete's first workout was just as bad as yours.

Your favorite chef's first meal was just as bad as yours.

Your favorite artist’s first work was just as bad as yours.

Keep going.

Each week, I do a deep-dive into the question of living meaningfully.

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