The Investing Shelf

Investing

A couple, a mortgage, and the patience it takes.

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Read the stories

Follow a person through it. Each book is a short series of chapters you can read or listen to.

OakwiseThe Long Game

Investing · Book 1

The Long Game

Priya & Marcus. A mortgage, kids, and time.

Expected Dec 2026

A couple with a mortgage, two kids, and an RESP they keep meaning to start. Investing isn't a hot tip or a lucky guess; it's patience, turned into a habit. The story of getting off the sidelines and letting time do the heavy lifting.

Chapter 1 Coming soon

The Money That Sits Still

Priya and Marcus earn well but their savings just sit in cash while they wait for life to calm down. They learn that staying on the sidelines is itself a costly choice.

Chapter 2 Coming soon

The Snowball Nobody Started

Simon sketches how money grows on its own when it has time, and why the years they have spent waiting were the most valuable ones they will ever have.

Chapter 3 Coming soon

Marcus Has a Hot Tip

Marcus is sure he can pick a few winners. Simon gently shows him why owning the whole market beats betting on pieces of it, and why timing rarely works.

Chapter 4 Coming soon

The Whole Market in One Fund

They discover that a single low-cost index fund can hold thousands of companies at once, giving them a complete, diversified portfolio without the guesswork.

Chapter 5 Coming soon

How Much Risk Can You Sleep On

With two decades until retirement and kids to think about, Priya and Marcus work out a stock and bond mix that matches their timeline and lets them sleep.

Chapter 6 Coming soon

The Silent Fee

Simon shows them the fee buried in their old mutual funds, and how a percentage that looks tiny can quietly swallow a huge slice of their savings over time.

Chapter 7 Coming soon

The Right Bucket for the Job

TFSA or RRSP? They learn to match each account to the goal and the tax break, so the same dollar invested ends up working harder.

Chapter 8 Coming soon

The Kids' Account They Kept Meaning to Open

The RESP they have put off for years turns out to come with a government grant they have been missing. They finally open it and start catching the match.

Chapter 9 Coming soon

The Set-It Habit

They automate a fixed amount on every payday so investing stops depending on willpower, and weigh doing it themselves against letting a robo-advisor steer.

Chapter 10 Coming soon

The Month the Market Dropped

The market falls and Marcus wants to sell everything. Simon helps them sit still, and they learn that staying invested through a scary stretch is the real skill.

Chapter 11 Coming soon

The Plan That Runs Without Us

A year on, their portfolio runs itself: automatic contributions, one calm rebalance a year, and a short annual check. The long game is finally just a habit.

OakwiseWhat's Left to Build With

Investing · Book 2

What's Left to Build With

Ray, 54 · Investing

Expected Jan 2027

What's still possible after the RDSP's best window has closed: the TFSA as the workhorse, the DTC refunds put to work, and a smaller fixed pool invested with care.

Chapter 1 Coming soon

What's Left to Build With

Investing on a fixed disability income is real but different. Ray starts from what's actually possible now, setting goals before products.

Chapter 2 Coming soon

The Window, One More Look

The RDSP grant and bond closed at the end of the year Ray turned 49. He names the loss once, without false hope, and moves on.

Chapter 3 Coming soon

The Account You Can Still Open

Ray can still open an RDSP and contribute until the end of the year he turns 59. There's no grant, but the tax-sheltered growth is real.

Chapter 4 Coming soon

The Workhorse

For most of Ray's plan the TFSA does the heavy lifting: flexible, tax-free, and well suited to someone in his position.

Chapter 5 Coming soon

A Smaller, Steadier Pool

A fixed income lowers how much risk Ray can carry. He invests a smaller pool conservatively, adjusting the usual time-in-market advice to fit.

Chapter 6 Coming soon

Putting the Refund to Work

The retroactive DTC lump sum is a one-time chance to fund the plan, not the wish list. Ray treats it as seed capital, not spending money.

Chapter 7 Coming soon

Cash You Can Reach

Ray keeps care money liquid. He sizes an accessible reserve around his health needs and learns what not to lock away.

Chapter 8 Coming soon

The Asset Test, Quietly

Where Ray holds money can decide whether he keeps AISH. TFSA and RDSP assets are exempt; non-registered investments may count, so structure matters.

Chapter 9 Coming soon

The 10-Year Catch

The RDSP holdback makes grants and bonds from the last ten years repayable on withdrawal. It's lighter for Ray, but the rule still shapes his timing.

Chapter 10 Coming soon

Build With What's Left

Ray assembles the plan: RDSP, TFSA, a conservative pool, and a liquid reserve, all AISH-safe. A modest plan that grows something is the win.

OakwiseThe Forty-Year Plan

Investing · Book 3

The Forty-Year Plan

The Whitfields · Investing

Expected Mar 2027

Open Owen's RDSP early, max the grant, capture the bond, and let a multi-decade horizon do the heavy lifting.

Chapter 1 Coming soon

Open It Early

The single most powerful move is opening Owen's RDSP while he's small. Time is the part the family can never buy back.

Chapter 2 Coming soon

The Government Matches You

The Canada Disability Savings Grant matches RDSP contributions, and matches lower-income families most generously, up to annual and lifetime caps.

Chapter 3 Coming soon

Money for Nothing

The Canada Disability Savings Bond pays into a low-income beneficiary's plan with no contribution required. The Whitfields open the RDSP regardless.

Chapter 4 Coming soon

Catching Up

Unused grant and bond entitlement carries forward. A single larger contribution can reclaim several past years of match at once.

Chapter 5 Coming soon

A Forty-Year Horizon

With four decades to grow, Owen's RDSP can hold growth investments, kept low cost and left alone to ride out everything in between.

Chapter 6 Coming soon

RESP or RDSP?

An RESP assumes school; the RDSP assumes a life. For a child who may not pursue post-secondary, the Whitfields weigh which assumption fits Owen.

Chapter 7 Coming soon

Moving the Money Over

If post-secondary never happens, RESP investment growth can roll into the RDSP under conditions. The bet isn't all-or-nothing.

Chapter 8 Coming soon

The Family's Other Buckets

The RDSP is for Owen's lifetime; a TFSA stays flexible and in the parents' hands. The Whitfields use both, on purpose.

Chapter 9 Coming soon

The Ten-Year Rule

The RDSP rewards a long horizon. Money pulled out early can claw back a decade of government help through the assistance holdback.

Chapter 10 Coming soon

The Machine Is Running

The RDSP is open, funded, invested, and capturing every dollar of match. The last job is making sure it survives the parents, leading to the estate plan.

OakwiseAutomatic

Investing · Book 4

Automatic

Jesse, 33 · Investing

Expected Apr 2027

The honest DTC application on mental-functions grounds, then set-and-forget investing that survives an inconsistent brain.

Chapter 1 Coming soon

The Form That Doesn't Believe You

The DTC is about how a condition affects daily life, not what it's called. Jesse learns an invisible condition can qualify on mental-functions grounds.

Chapter 2 Coming soon

Impact, Not Diagnosis

Jesse learns how T2201 actually works for ADHD: the mental-functions category, describing functional impact honestly, and the medical practitioner's role.

Chapter 3 Coming soon

When They Say No

A no on the DTC is often not the end. Jesse learns how often claims are refused, and how the review and appeal path works, with many approvals coming the second time.

Chapter 4 Coming soon

The Window That's Still Open

Qualifying young means the RDSP's matched government money is still on the table. This is the door Ray's age closed, and the centrepiece tool for Jesse.

Chapter 5 Coming soon

Free Money, Matched

The government matches RDSP contributions and may pay in for free through the bond. With carry-forward catch-up, it's the best-return move few have heard of.

Chapter 6 Coming soon

One Fund, On Repeat

One diversified asset-allocation fund, bought automatically, beats a clever portfolio Jesse stops maintaining. Low-decision investing survives an inconsistent brain.

Chapter 7 Coming soon

Set It and Forget It

Automatic contributions into the RDSP and TFSA remove the one step willpower keeps breaking. Fewer accounts and fewer decisions, deliberately boring.

Chapter 8 Coming soon

Don't Touch It

The biggest threat to Jesse's portfolio is the urge to mess with it. Built-in friction protects a long-horizon plan from a novelty-seeking brain.

Chapter 9 Coming soon

The Accommodation

For an executive-function disability, automation isn't a convenience, it's the accommodation that makes the plan possible. The Freedom app earns its moment here.

Chapter 10 Coming soon

Building With Both

With the DTC unlocked and contributions automatic, the RDSP and TFSA build wealth in the background. Now Jesse points it at the long horizon.