E26: The Pay Now Play Later Philosophy: Balancing Being and Doing - with Josh Thiessen

Can You Plan for Tomorrow Without Missing Today?

For many of us, life feels like a tug-of-war between responsibility and presence. We work hard to secure tomorrow but risk missing today.

This week, I sat down with my son, Josh Thiessen, to talk about his “Pay Now, Play Later” approach — a philosophy that prioritizes discipline and preparation but sometimes leaves little room for rest or joy in the moment. It’s a mindset that serves him well in planning for the future… but is it possible to hold that vision while still being present?

The Upside of “Pay Now, Play Later”

There’s no question that future-focused living has benefits:

  • Security and stability: Planning ahead helps avoid financial and emotional chaos.

  • Clear goals: A disciplined approach keeps priorities front and center.

  • Delayed gratification: Learning to wait often leads to deeper satisfaction later on.

But there’s a cost when life becomes all about the next milestone — the joy of today can slip through the cracks.

The Case for Balancing Being and Doing

Living only for tomorrow can leave you disconnected from what’s happening now — from relationships, rest, and simple pleasures. On the other hand, living only in the moment can make it hard to prepare for the future you want. The sweet spot? Learning to hold both:

  • Create space for pause. Schedule moments to rest and enjoy life as intentionally as you plan for the future.

  • Check in with your “why.” Future planning is easier to balance when you remember what you’re working toward.

  • Redefine productivity. Sometimes, rest is the most productive choice you can make.

Try This at Home: The Balance Audit

  1. Look at your week and count how many hours are spent on “future-focused doing” (work, planning, saving).

  2. Now count how many hours are spent simply being (relaxing, connecting, enjoying).

  3. Ask: Does this ratio feel right to me?

  4. If not, choose one way to add more presence into your week — even five minutes of mindful pause can shift everything.

The takeaway: You don’t have to abandon discipline to enjoy the present, and you don’t have to abandon presence to build a better future. Real freedom comes when you find a rhythm that honors both.

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E27: Break the Pattern: A New Approach to Holiday Gatherings

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E25: Finding Freedom in LESS: Is Minimalism the Path to Your Well-Being? - with Brian Gardner