Why Midlife is the Perfect Time to Regret-Proof Your Life!

midlife blog empty nestI think that your midlife is actually the best time to regret proof your life.


Because you’re older and wiser. Simple as that.

Here’s what I mean by regret-proofing.

Regret-proofing is what you can do ON PURPOSE to make sure that you don’t have regrets in your life.

See what I mean? As women in the middle, between 40ish and 60ish, I know that you know that you definitely do not want to have regrets. And also, even if you don’t feel it all the time, you really are older and wiser. Big milestone birthdays, special family events, taking care of elderly parents  and the whole empty nest thing all make regret-proofing pretty compelling at this age.

I write this with complete confidence.

And, another thing I’m pretty sure about is that you will end up regretting having regrets.

Regret-proofing is about avoiding this.

Trust me on this one.

I’m not talking about regrets that you may have already.

I’m talking about the ones that you don’t yet have, and really don’t want. You are probably starting to think about them. You might even be a little afraid of having them.

The concept of regret-proofing is that you want to do everything you can to make sure you don’t have regrets.

That you live your life exactly the way you want to live it.

That you’re excited about your plans for the future.

That you’re living with intention. Just like Oprah would say.


You. Living intentionally.

The million dollar question is, how do you do that?

I have to say, this concept is at the core of the work I do with my clients.

In fact, my signature program is called 9 Steps to Regret Proof your Life. I absolutely love this concept.

The reason is because there’s so much you can do with this work.

It’s totally possible to reduce the likelihood of you having regrets.

And guess what?

It all starts with your thoughts and your awareness of them.


It’s not some mysterious luck machine out there in the universe. That if you’re lucky, you don’t have regrets and if you’re unlucky, you do.

It’s not like that.

It’s your thinking.

Learning how to identify thoughts and see that they’re optional is the very first thing you need to do.

I’m not going to go into all 9 Steps right now in a blog, don’t worry. But, I do see the bulk of regret-proofing falling into three areas of thought work.

The first is around your contribution. What I mean is the way you want to contribute professionally, either for compensation or as a volunteer.

So many of you have been in jobs way too long,or are just plain ol’ bored with what you’re doing.

This is what I mean. The way you contribute takes up a fair bit of time every day, every week, every year. So it’s really an important chunk of your life to be intentional about.

What i see with my clients is that, as women in the middle, time just goes by and before you know it, decades have gone by without a lot of reflection and planning about this part of your life.

You like stability. You like your benefits. You like routine.

I get it. But…for now, just please be open to the idea that for regret-proofing purposes, you gotta take some time and really think this stuff through.

Another big part of your life that needs some serious regret-proofing attention is your relationships.

Again, as women in the middle, you’ve been rushing around in a chaotic blur for a couple of decades. It’s hard enough to deal with life, let alone the quality and nature of the relationships you have in your life. Thinking about if they’re what you want going forward is the next step. This is a huge area of potential regret for my clients.

I’m not just talking about your spouse or partner.

I’m also talking about your

  • kids
  • parents
  • friends
  • siblings
  • neighbors
  • cousins
  • colleagues.

Are you the person you want to be in these areas of your life?

Might you have regrets if you don’t make some changes and start visiting people in the hospital, find time for lunch, organize that girls trip, spend one on one time with each of your kids, pick up the phone for birthday calls?

If you don’t want to have regrets about your relationships, you have to be more intentional about them, prioritize them and do some serious regret proofing.

The third area of regret-proofing your life is your relationship with yourself.  I think you might get this one pretty quickly. This has to do with making sure that you don’t have regrets about YOU – and I mean things like your weight, your health, your skills, your experiences.

So, where do you want to travel in your life time?

What do you want your weight to be?

What skills do you want to have to have more fun, like music, yoga, art, dance?

What experiences do you want to have?

Do you want to live more in the present moment?

Do you want to write?

These things take time, focus, planning and accountability. And if you don’t put in the effort, another decade or two will fly by and you may have regrets.


Think to yourself for a minute. What would your future self say to you right now when it comes to regret-proofing?

What does she know you should be doing, because you want to? So you won’t have regrets?

Allow that thought.

Don’t squish it down or try to kick it out of your brain.

Listen for mind chatter and drama that it’s too hard, too expensive or will take up too much time.

  • What did she just say to you?
  • What did she whisper into your ear?
  • What does she know you need to do so you don’t have regrets?

Listen to her.

Your future self knows you can do hard things.

She knows that you’re worth it.

She doesn’t want you to have regrets.

Neither do I!

So ladies, who’s in?  I think it’s time to regret-proof your life.

I hope this perspective helps you as you take a baby step toward committing to this most important act of self-care.

Download for free: Regret-Proofing your Vision Worksheet.  Perfect to start to think through and visualize what you really want to create in your life! Great way to start a vision board too!



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