The Simplicity Sessions
The Simplicity Sessions
Jenn Pike
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#585: The Simple System for Building Wealth
45 minutes Posted May 21, 2026 at 10:00 am.
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This week, Chris and I are sitting down together to talk about one of our favorite topics: building real, sustainable wealth without the overwhelm.

If you've ever felt like you're behind, like it's too complicated, or like you just don't know where to start — this episode is for you.

 

What We Cover:

We break down the four pillars of wealth that Chris uses with his clients every single day:

  1. The Safety Pillar — Your emergency fund. This is priority number one. We talk about why three to six months of expenses matters, what that actually looks like for your life (hint: it's different for everyone), and the magic of just having enough to sleep at night.

  2. The Future Pillar — This is your retirement strategy. RRSPs, TFSAs, first home savings plans, permanent life insurance — we break down why diversification here is non-negotiable and why the tax strategy behind your withdrawals matters just as much as the saving itself.

  3. The Freedom Pillar — Our favorite one to talk about. This is where your money starts working for you — rental income, dividends, non-registered investments — the assets that buy back your time and give you options. Could you retire earlier than you think? Maybe.

  4. The Legacy Pillar — What do you want your money to do after you're gone? We get into wills, estate planning, life insurance, and charitable giving — and why taking care of yourself first is actually the most loving thing you can do for the people you leave behind.

 

We Also Talk About:

  • Why building wealth is honestly kind of boring (and why that's a good thing)

  • The stats on why women tend to outperform men as long-term investors

  • Why lottery winners go broke (and what that teaches us about money mindset)

  • The most common wealth-building mistakes: starting too late, keeping cash under the mattress, spending your raise before you get it, not having a will, and trying to time the market

  • Opportunity cost — why your daily latte isn't the villain, but your intention behind it matters

  • How Chris breaks down $1,000/month across all four pillars (a simple rule of thumb you can actually use)

  • Why your definition of financial freedom might be different from your partner's — and why that conversation is so important

 

Questions to Ask Yourself After This Episode:

  • Which pillar am I strongest in right now?

  • Which pillar needs the most work?

  • Do I have a will? Do I have life insurance?

  • What does financial freedom actually look like for me?

  • What's one thing I can do this month to strengthen my weakest pillar?

 

Let's dive in!

Thank you for joining us today. If you could rate, review & subscribe, it would mean the world to me! While you're at it, take a screenshot and tag me @jennpike to share on Instagram – I'll re-share that baby out to the community & once a month I'll be doing a draw from those re-shares and send the winner something special!

Click here to listen:

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Spotify – CLICK HERE

This episode is sponsored by:

  • withinUs | Use the code JENNPIKE20 at withinus.ca for a limited time to save 20% off your first order and 20% off your first subscription order

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Have a question? Send it over to [email protected] and I'll do my best to share helpful insights, thoughts and advice.

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