How to Support Yourself Through Change With One Powerful Question

Let’s talk about change and transition.

Maybe you’re starting the new year.

Perhaps you’ve set new goals for the quarter.

Maybe you’re beginning a new job.

Or you’re moving to a new location.

Each one of these experiences offers a chance to check in with yourself.

It provides the opportunity to decide intentionally what you want to bring with you to the next chapter of your life.

And what you want to leave behind.

Making these powerful decisions can be a life-changing experience.

And on episode 129 of the I’m Busy Being Awesome podcast, I share one question that’s helped me create just that.

This one question has guided my decisions and helped me transform my life in ways I never thought possible.

And today I invite you to think about your life and the transitions you’re navigating.

Ask yourself, “how do I feel about each one, and why?”

Then, check out episode 129 of the podcast.

Learn this powerful question.

And consider it for each area of your life as you move through your transitions with even greater confidence.

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

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

In This Episode, You Will Discover… 

  • One powerful question to help you make changes and transitions with greater ease
  • Three reasons why this question can help you grow in clarity in confidence
  • How you can apply this question to your own life for powerful growth

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Episode #129: How to Support Yourself Through Life Transitions With One Powerful Question (Transcript) 

You’re listening to the I’m busy being awesome podcast with Paula Engebretson episode #129.

Hello friends. Welcome to the podcast. How are things going? I’m recording this episode in the last week of 2021. It’s that time of the season when I tend to do a lot of reflection. I love to spend time looking back on the previous year and ahead to what I want to create. And more specifically, what I want to create while living into my word of the year, which I mentioned back in 127 is possibility.

And last night I had a call with my friend Jenn, and we each shared our goals and plans for the year ahead. As we spoke, I shared with her a question that I love to ask myself. It’s also one that I’ve explored with clients frequently over the last couple of weeks. And it’s a question that I think is really effective at any time of transition or new beginning in your life. Whether you’re starting a new year, shifting into a new quarter, beginning a new job, moving to a new location, etc.

I heard the question first posed by Brooke Castillo, and it really changed the way I think about fresh starts generally. And that question is: would I choose this again? Knowing what I know now, and knowing where I am now, is this something I would choose again going forward in my life?

And today we are going to dig into this question. I’ll share the reasons why I find this question so powerful in multiple situations. I’ll offer some of my own examples of times this question really helped me make strong, confident decisions as I approached fresh starts in my life. And then we’ll talk about different ways you might consider using the question in your life whether you are listening to this in real-time and thinking about fresh starts in the year ahead, or whether you’re listening to this on a random Tuesday in April and you have a personal fresh start going on in your life.

Would I Choose This Again?

So, as I mentioned, there are several reasons why I really love to ask this question both for myself and when I’m talking with clients. First, when you ask yourself, “would I choose this again?” It provides a powerful opportunity for you to slow down and reevaluate what’s going on in your life. And it offers that important reminder that you can redecide at any time.

Would I choose to be part of this committee again? Would I choose to buy this kitchen appliance again? Or would I choose this friendship again? Would I choose to keep this hobby or participate in this club again? Yes or no?

I think it’s easy for our black and white all-or-nothing brains to think that once we’ve made a decision, or purchased a product, taken a job, or agreed to be on a committee or a team, we are stuck with it forever. We tend to think, I can’t change my mind. I’ve already made a commitment. I already made an investment. I’ve already put in so much time. I can’t possibly change now. That would be wasteful. That would be irresponsible. People would judge me for changing my mind. 

And because we tell ourselves different versions of this story over and over, we allow ourselves to stay stuck. We keep settling for what is. And we don’t challenge our mindset. We don’t consider the fact that things can absolutely change. So again, this question: would I choose this again? It really reminds us that there is – indeed – a choice. There are options available. You have the option to re-decide whether you’d choose it again.

Create Clarity

This question also creates a lot of clarity for our brain. And this is especially true when you ask yourself the question about something that might feel a little heavy or charged. Maybe it’s about a job or a boundary you’ve established. If you struggle with people-pleasing, maybe it’s somewhere you’ve always said yes, but you really want to say no. When you ask the question – would I choose this again – and you are willing to sit with that question, it can be quite eye-opening to notice your gut response. It can be telling to notice one way or another; would I choose this again? Yes, I would. Or would I choose this again? No, I wouldn’t. Whatever your immediate response, it’s really good to know.

Now, I also want to mention that you don’t need to act on that answer immediately. If you ask yourself, “would I choose to continue saying yes to this role at work?” And your gut response is no. That doesn’t mean you have to go to your boss and tell them you’re no longer willing to fulfill that role any longer and if they aren’t okay with it, you’ll quit immediately. 

I’m not saying you have to act right away. And for my ADHD out there, be aware of our struggle with impulse control. That desire to act immediately. Instead, we want to tune into that awareness and insight of what’s true for you. This is very empowering in itself. And when you give yourself time to be intentional about it, it has the potential to set things in motion to help ensure you are moving in the direction you want at a pace that feels safe and comfortable for you.

Again, I especially love to ask this question during times of transition. So whether it’s moving houses, beginning a new job, the start of a new school year, or in this case the beginning a new calendar year. Asking this question helps foster starting fresh with a clean slate. A clean slate of commitments, of belongings, of decisions that you’ve intentionally brought with you into the new year.

Strengthen Confidence

And the third reason why I think this question is so powerful. The third reason why I invite you to start asking yourself, would I choose this again? Would I agree to this again? Or would I buy this again? And answering that question honestly. Is doing so can help strengthen your confidence in your decision. It checks in with where you’re at now and reconfirms the decisions you’ve made and the life you’ve chosen. Because again, you did so with intention. You made your decision with intention.

For example, let’s say last year you decided to write a book, and you still have more to do this year. Then perhaps this year, you re-evaluate and you ask yourself; would I choose this goal again? Would I choose to do this again and continue onward? 

Maybe your gut response is yes. I would choose this again. I would choose to continue on this journey of writing my book. If this is the case, knowing this information is so powerful the next time you hit a stumbling block and your toddler brain freaks out. When that immediate reaction comes up when something goes “wrong,” and your toddler brain thinks, why are we still doing this? This is such a waste of time. I’m never going to finish this book. It’s never going to become reality. You can remind yourself, “it’s okay, brain. Remember, we chose this. We intentionally chose to do this again. This is just one of those hard parts. But I signed up for the hard parts. We can re-evaluate next quarter or next year. But right now, we’ve committed. We chose to do this again.”

So, it really works both ways. By asking yourself this question, “would I choose this again?” You’re offering yourself the freedom to release the things you no longer want. And going forward, you’re also giving your brain the additional support and reassurance to stick with it when things get hard. Because you know you chose ahead of time with your prefrontal cortex – the executive part of your brain – that you do want to stick with it. You did indeed choose it again.

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Now so far, I’ve been speaking a bit in the abstract. And I know for my brain it can be hard to put concepts into context when I don’t have any concrete examples. So, I thought I would share three different examples in my life where I have used this question to help release that extra baggage – both mentally and physically. And further, to help create more clarity in my life. And I tried to choose three very different scenarios to demonstrate how adaptable this question is.

So the first example aligns with decluttering and simplifying my space. In fact, I return to this question basically each season when I go through my clothes or different areas in my house. I ask myself: would I buy this again? In other words; would I buy this coat again? Would I buy this sweater again? And would I buy these shoes again? If the answer is no, then there is no reason for me to keep it. Especially if I’m not using it.

More recently, I’ve used this question to help me sort through different books and resources and notebooks and information that I’ve gathered over the last many many years. And I will talk about a little bit more in correlation with my next example. But first, I invite you to think about an area of your home or your office. Your physical space generally. Maybe it’s a closet or your basement.

As you think about that area and the items within that area, ask yourself: would I choose this again? Would I buy this again? And if it was a gift or something that’s been passed on to you. You can ask yourself, would I buy this at all? Would I choose to have this intentionally? 

If the answer is no, and especially if you’re not using it, this is a great opportunity to donate those items. And if they’re not in good condition, recycle them or throw them out. And again, your brain will want to fight this. It will think, but it’s in good condition. Or it’s brand new; I never even used it. Or it was so expensive. 

Again, if you wouldn’t buy it again today, you don’t need it now. Remember, we are starting fresh. We’re starting with a clean slate. This is a beautiful opportunity to release those items you don’t want to take with you into the new year or the new season of life.


Another powerful area where I used this question in my life was my career as a professor. As I mentioned, over the last six months or so I’ve been going through a lot of books and resources and information, and asking myself, would I buy this again now? Would I choose this again? And the reason behind this examination is that I left my university position at the end of July and I’m going through all of the textbooks and resources I’ve collected over the last many years.

And if you’ve ever made a career change yourself – you know this can be a big decision. Or at least my thought was, “this is a huge decision.” And it’s one that I did not take lightly. In fact, over the last several years I asked myself the question, “would I choose this job” each semester. I would check in with myself and ask, “would I choose this again?” And for each of those semesters until January 2021, the answer was yes; I’d choose this again. I love what the job offers. I love the opportunities I have to work with incredible students. And I still have areas of growth for myself within this role.

So, every time I asked myself that question, “would I choose this again?” The answer was yes. And that was my confirmation: yes, I’m choosing this. And I’m choosing it with intention. I want to be here. I want to do this work. Even when it’s hard, this is what I’ve chosen.

And then finally last year in December of 2020 and January of 2021, I asked myself the same question: Would I choose this position again? And this time the answer was no. I would not choose this role again. Instead, I knew I wanted to shift into coaching full-time. I knew that’s where my strengths were. That was where I see myself serving the most people and making a bigger impact. And again, I did not take this question lightly. It wasn’t a flippant decision that I decided overnight and quit the next day. I took time to reflect. I got loooooots of coaching. And I finished out the school year.

But by giving myself that opportunity to reflect on the position. And by knowing that I’d done this reflection in the past with the answer being “yes,” and this time the answer was “no,” It was a reminder to lean into that truth. It was a reminder that I was at another transition period in my life. And I was ready to step into the next stage of growth with courage and uncertainty and fear and joy and doubt and trust and an entire amalgamation of emotions that often accompany change for me. And I made that shift.


And then the third area where I have used this question: would I choose this again? Is one that I’m currently still in. I thought it might be helpful to share an example where I’ve not made the full transition yet. I’m still doing the work. And this is regarding where I live. 

I currently live on the East Coast in Massachusetts. And I’ve been out here since 2007 when I started grad school. That’s over 14 years, which is insane to me. But recently, especially over the last couple of years, I’ve noticed that pull to move back home to Minnesota where I’m from originally. And when I asked myself, would I choose to continue living here? I found the answer was no, I would not. I would instead choose to live in Minnesota. 

Now again, this is not something I’m acting on immediately. I’m not putting the house up for sale and moving tomorrow. But having that gut check. And knowing deep down that I’m ready for this change. It allows me to start thinking ahead. It allows me to start putting plans in place and wheels into motion to make this next goal a reality in the coming future. So again, this is one that’s not all ironed out yet. It’s not wrapped up with a beautiful bow. And I know there will be obstacles and messiness along the way. But after 14 years of living out on the East Coast, I’ve come to a place of realization that going forward, I’m ready for a change. And that’s good to know.

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And it also brings up a really important point that I want to stress here. So if you’re multitasking or you’ve lost focus, come back. Really listen to this point. Just because you would not choose it again, doesn’t mean it wasn’t a beautiful decision and a powerful experience at the time. It doesn’t mean you have to regret choosing it before. Instead, it simply means that you have grown and you’re ready for the next stage. 

So for example, if I’m getting rid of clothes that I would no longer choose again, I don’t regret that I bought them. I don’t regret that I wore them. I’m glad that I did. But going forward, I’m ready to let them go. 

Similarly, I wouldn’t trade my grad school and academic life for anything. The amount of both personal and professional growth that I experienced during those 14 years is absolutely life-changing. And in fact, it was during that time that I got my ADHD diagnosis, and I probably wouldn’t have gotten the diagnosis if I wasn’t in the role I had. So again I don’t regret it. In fact, I value every moment of it. Every challenge, every connection made, every conference talk given, and paper published. It all played such an important part in getting me to where I am now. 

But then I got to a point where I was ready for a shift. I was ready for the next step in my journey, and it was time to release that first decision and choose something new. And the same goes for my home. I love my home. I love where I live and I love the memories I’ve built with Ryan and our little fur babies. And, we’re ready for that next step of the journey as well. And while we don’t have the exact timeline yet, that’s okay. What we do know is the next choice we make is moving back to Minnesota. And that’s good to know.

So whenever you are listening to this, I invite you to think about an area in your life. Maybe it’s an area that feels a little sticky. Maybe it’s an area that’s a little cluttered. Or maybe it’s a part of your life where you frequently feel overwhelmed thinking about everything that’s involved. 

This week, I encourage you to breakdown the components of that area. Whether it’s the things in your basement, a project you’ve agreed to take on at work, a relationship with a friend or a coworker, a certain lifestyle you’ve established etc. Ask yourself, would I choose this again? And listen for that answer. 

If the answer is yes, you would choose it again. Hold that tight. Use that as further reassurance and confirmation that you’re doing what’s in alignment with you. And if the answer is no, again, you don’t have to take action right away. But now you have greater clarity with regard to where you’re at and what you truly want.

And frankly, I think that a lot of us are facing these moments of growth and change right now –  not only with the new year, but with our world as a whole. And that’s one of the reasons why I felt inspired to share this episode with you today. So I invite you to ask yourself the question and then give yourself the space and the grace for contemplation. Give yourself the time to lean in and listen. Would I choose this again? Because each time you ask and answer, you’re one step closer to living that life you want.

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