‘Someday’ Isn’t a Day of the Week

For those thinking about (or already in) retirement

🟢 How many times have you said “someday”?

Someday I’ll travel more. Someday I’ll get back into that hobby. Someday I’ll slow down and actually enjoy my life.

Sam Horn, CEO FORCE FOR GOOD wrote a whole book called Someday is Not a Day in the Week and not only is it a great book but she is right! ‘Someday’ is the most popular destination nobody ever actually gets to!

And, believe it or not, accomplished, driven people are often the worst offenders. We’re so good at executing on other people’s timelines that we never get around to building our own. It stays sitting on the ‘someday’ list.

🧭 Here’s where it gets tricky:

I wrote about this before… people spend decades delivering on deadlines that matter to everyone else. The quarterly report, the board presentation, the product launch, the fundraiser… and they’re excellent at it.

But when it comes to their own next chapter? Suddenly everything is vague. “I’d like to do some travelling.” “I’d like to see if I can make homemade Adirondack chairs or sheds to sell in my retirement.”

However, those are dreams, not plans and I think dreams need a little more than good intentions to actually happen.

Knowing what you want and actually doing something about it are two very different things. Most people stop at the first one and wonder why someday never comes.

🌱 Vague plans have a way of staying vague.

In my book, I talk about a tool borrowed from Lean thinking called the A3, which is a one-page problem-solving framework that forces you to get specific. What’s the real gap between where you are and where you want to be? What’s actually holding you back?

It sounds simple, but what comes up when you actually work through it often surprises people.

One of my clients had been saying for three years that she wanted to start a small business after she retired. When we worked through it, the real blocker wasn’t money or a shortage of ideas. Instead, it was that she’d never given herself permission to take it seriously and never thought beyond the first step. She felt like she’d have time to think it all through ‘someday’ and never considered the runway it takes to get there.

💡 Someday becomes real the moment you give it a date.

Not a vague “in the next year or two.” An actual date…a first step…something small enough to do this week that moves you an inch closer to the thing you keep putting off.

My dear client, Gloria, has been telling herself that ‘someday’ she will restart yoga. She decided it was best to get back into it in the privacy of her own home using a video rather than the larger effort it took to book herself into a class at a studio across the city. Her first step though was even smaller, she decided to watch the yoga video first, get her equipment in place and re-familiarize herself with the yoga poses. This was on Monday. Her plan on Tuesday morning, after her husband went to work, was to complete the yoga video…and she did it! She sent me a text later saying, “It was great! It felt good, and my body and mind responded so well.”

We don’t have to have it all figured out before we start and we don’t have to take big leaps into the yoga studio right away.

Here’s what I’d like to leave you with. We should all stop treating your own future like it’s the lowest priority. Let’s get it off of the ‘someday’ list!

✍️ Something to reflect on this week:

What’s the one thing you’ve been saying “someday” about?

The next question I have for you is: what would the smallest step look like so you could do that one thing before the end of the month?

If you’re ready to stop waiting and start designing, my book gives you the tools to do exactly that. Designing Your Second Act: How to Create Meaning and Confidence Beyond Full-Time Work is available now at www.routledge.com

See below for a 20% off discount… just for my subscribers! You’ve got this!!

And please, if you know someone who’s been living in “someday” for a while? Feel free to send this article their way. 🙏