I’m Saving Aggressively and Missing Out on Life

Money Dilemmas is where we talk about the tricky stuff - the conversations about money that live in the grey area between love, power, fairness, and everything in between.

Each story starts with a real member dilemma, the kind many of us have quietly wrestled with but rarely said out loud.

Because money isn’t simply transactional; it’s about what we value, what we tolerate, and what we’re taught to accept.

And at the end of every story, one of our co-founders weighs in - offering her two cents and best advice on how to navigate the dilemma.

The Dilemma

I’m 58 and, on paper, I’m doing everything right. I save diligently, I’ve paid down most of my mortgage, and I’m very focused on making sure I’ll be okay in retirement.

I grew up watching my parents worry about money, and I promised myself I’d never put myself in that position.

The problem is, my life feels like it’s permanently on hold.

I say no to trips because they feel indulgent. I hesitate before dinners, shows, weekends away. Friends talk about travelling while they’re healthy, and I tell myself I’ll do that later, when things feel more “secure.”

But later keeps moving further away.

I’m healthy now. I have energy now.

And I’m starting to notice how often I choose the sensible option over the joyful one.

Sometimes I wonder who I’m saving all this money for if I’m not actually living while I can.

At the same time, the fear is real. I don’t want to be older and anxious, watching every expense, wishing I’d been more careful.

Financial security matters deeply to me, and I’ve worked hard for it.

I just don’t know where the line is.

When does being responsible turn into being overly cautious?

And how do you give yourself permission to enjoy life without feeling reckless?

I’m scared of two futures: one where I run out of money, and one where I realise too late that I ran out of time.

Camilla’s Take

Thank you for sharing this. I think many women recognise themselves in what you’ve written, especially those who’ve spent a lifetime being careful, independent, and financially responsible.

One of my favourite books is Die With Zero by Bill Perkins, and I really recommend it in moments like this.

The idea isn’t about spending wildly or being irresponsible. It’s about understanding that money has the highest value when it’s used at the right time in your life.

He talks about “time buckets,” meaning that different experiences belong to different stages of life.

Certain trips, physical adventures, and freedoms are much harder, or simply less enjoyable, later on, no matter how much money you have.

Saving everything for a future version of yourself can mean missing the window where that money would actually bring the most joy.

What struck me most is how disciplined savers often keep moving the goalposts.

First it’s once the mortgage is lower.

Then once there’s more buffer.

Then once retirement feels closer.

There’s always another reason to wait, and meanwhile life keeps moving.

This doesn’t mean ignoring risk or abandoning the security you’ve built. It means being intentional.

Asking yourself what “enough” really looks like, and what the cost of excessive caution might be. Running out of money is one fear, but running out of time is another.

You’re healthy now. You have energy now.

There are experiences this version of you can enjoy in a way an older version might not, even if she has more money. U

sing some of what you’ve saved today isn’t a failure of discipline. It’s allowing your money to support your life, not just sit there protecting a future that never quite arrives.

You’ve already done the hard part. You’ve built stability.

Maybe the next chapter is about letting that stability work for you.

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