Don’t Save Your Life for Someday

This past weekend, I took a three-day trip with a friend who was celebrating her 70th birthday.

She had raced cars before, and for her milestone birthday she wanted to get behind the wheel and drive around Watkins Glen, a legendary racetrack in upstate New York.

So she did. At 70. At 140 mph.

I loved watching her give herself permission to do something she genuinely wanted to do to celebrate her special day.

She didn’t say, “Maybe next year,” or “Maybe I’m too old to do something like this.”

She just got in the car.

I couldn’t help but think about how many of us are still waiting for “someday.” How many of us are waiting to get in that car, so to speak, and do something we’ve always wanted to do?

We hold on to more than things

As The Downsizing Designer, I spend a lot of time helping people decide what to do with their belongings. But I’ve learned that downsizing is rarely just about stuff.

Rita’s video thumbnail: How to Downsize After 30 Years in the Same House (8 Steps) — How to Downsize After 30 Years in the Same House (8 Steps)

Sometimes we’re holding on to a house because it represents the years we raised our children there.

Sometimes we’re holding on to rooms we no longer use because letting them go feels like admitting that chapter has ended.

Sometimes we’re holding on to possessions because they remind us of who we used to be. And sometimes we’re simply holding on because changing anything feels too frightening.

But here’s the question I want you to consider:

Is what you’re holding on to helping you live the life you want right now, or keeping you attached to the life you once had?

Please think about that.

Giving myself permission

I’ve been out on the skinny branches myself many times. In 42 years of owning a company, I’ve taken many risks that scared me.

But on one particular adventure a few years ago, I gave myself permission to do something that scared me: I booked a 30-day trip to the south of France.

With a ticket to get there, a ticket to come home, and nothing planned in between.

I did that intentionally: no fixed itinerary and no reservations for every night.

And yes, it was a little scary sometimes. But it was a good scared. The kind of scared that tells you you’re stretching beyond your familiar comfort zone and discovering what you’re capable of.

I remember thinking, “If I don’t do this, I may spend the rest of my life wondering what would have happened if I had.”

That trip became one of the greatest experiences of my life. So far!

The regrets aren’t always about what we did

We tend to think of regret as something that comes from making the wrong decision. But sometimes regret comes from not making any decision at all.

Not taking the trip. Not learning something new. Not moving somewhere different. Not calling that person. Not saying yes. Not saying no.

Not making the change because we were waiting for the perfect time.

The truth is, there will almost always be a reason to wait. And at some point, waiting becomes a decision, too.

So I’ve come to think of my life in three separate categories.

What will I keep?

The people, the memories, the traditions, the possessions that genuinely matter. The things that support the life I want now.

What will I pass on?

The stories, the recipes, the photographs, the wisdom, the family treasures, the lessons I’ve learned along the way.

What will I finally enjoy?

The good china in that cabinet. The silverware in that drawer. The good bottle of wine you’ve been saving. The trip you’ve been talking about for 10 years.