The Retirement Shelf

Retirement

Leaving work without leaving life behind.

All retirement posts

Read the stories

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

OakwiseWinding Down

Retirement · Book 1

Winding Down

Joanne, 61. Am I going to be okay?

Expected May 2027

Joanne can see the finish line, and it worries her more than she lets on. Turning a lifetime of saving into a paycheque you don't outlive is its own skill. A story about leaving work without leaving life behind.

Chapter 1 Coming soon

The Question That Keeps Her Up

After thirty years of saving, Joanne faces the opposite question: not whether she is putting enough away, but whether what she has will actually last.

Chapter 2 Coming soon

Counting What's Already There

Simon helps Joanne add up what a year of retirement really costs, then work backward to the number she actually needs, replacing dread with arithmetic.

Chapter 3 Coming soon

The Cheque That Grows If You Wait

Joanne weighs taking CPP early against waiting, and learns that delaying buys her a bigger, inflation-protected cheque that lasts the rest of her life.

Chapter 4 Coming soon

The One That Can Be Clawed Back

Old Age Security arrives with a catch: earn too much and part of it is recovered. Simon shows Joanne how to keep her income under the line.

Chapter 5 Coming soon

The Help She Didn't Know to Ask About

Because she is single and her income is modest, Joanne may qualify for the GIS, a monthly top-up she had never heard of and almost left unclaimed.

Chapter 6 Coming soon

When the Savings Become a Salary

Joanne learns her RRSP cannot stay an RRSP forever. Simon walks her through converting it to a RRIF and the minimum it must start paying her each year.

Chapter 7 Coming soon

Which Pocket First

With money in a RRIF, a TFSA, and a regular account, the order Joanne draws from matters. The right sequence can save her years of tax.

Chapter 8 Coming soon

Spending It Without Running Out

Simon explains a sustainable spending rate and why a bad market in the first few years is the real danger, so Joanne can spend without fear of the well running dry.

Chapter 9 Coming soon

A Paycheque You Can't Outlive

To cover her essentials no matter how long she lives, Joanne considers turning part of her savings into a guaranteed income with an annuity.

Chapter 10 Coming soon

Leaving Work, Not Life

With the money settled, Joanne faces the part nobody warned her about: health, time, and purpose. A good plan, she sees, funds a life, not just a balance.

OakwiseThe Horizon, Recalculated

Retirement · Book 2

The Horizon, Recalculated

Ray · Retirement

Expected Jun 2027

CPP-D becomes a retirement pension, OAS and GIS enter, and Ray plans decumulation around ongoing care — and leaving things tidy for his daughter.

Chapter 1 Coming soon

The Horizon, Recalculated

When working life ended early, retirement planning becomes income planning for a long stretch. Ray reframes what the next decades need to fund.

Chapter 2 Coming soon

The Pension That Was Already Paying

At 65 Ray's CPP-Disability converts to the CPP retirement pension. He plans for the switch rather than being surprised by it.

Chapter 3 Coming soon

The Government Adds a Floor

OAS begins at 65, and GIS may follow for low income. Ray learns how they layer onto his new CPP retirement pension and claims everything he's owed.

Chapter 4 Coming soon

When AISH Steps Back

At 65 seniors' benefits take over from AISH. Ray maps the handover so the income mix is reshuffled cleanly and nothing falls through.

Chapter 5 Coming soon

Turning the RDSP On

Ray's RDSP disability assistance payments begin. Only part of each payment is taxable, and often at a low rate, so timing matters.

Chapter 6 Coming soon

Spending It Down, Carefully

Decumulation has to budget for care. Ray sequences his withdrawals and builds ongoing health costs into the drawdown, not around it.

Chapter 7 Coming soon

Keeping It Simple for Nicole

Ray names beneficiaries on his registered accounts and keeps the estate uncomplicated. Clarity is the kindest thing he can leave his daughter.

Chapter 8 Coming soon

The Conversation You Don't Want

A plan for if one day Ray can't decide is part of retirement, not separate from it. He revisits the advocate he named back in the budgeting book.

Chapter 9 Coming soon

A Smaller, Calmer Horizon

Pensions, GIS, RDSP payouts, and a reserve come together. Recalculated and smaller, Ray's retirement is still calm and intentional.

OakwiseAfter We're Gone

Retirement · Book 3

After We're Gone

The Whitfields · Retirement

Expected Jul 2027

The question every such parent carries: the Henson trust, RRSP rollovers into the RDSP, and a care plan for a child who will outlive his parents.

Chapter 1 Coming soon

Both, Not Either

The parents can't trade their own retirement for Owen's security or his for theirs. The plan has to hold both horizons at once.

Chapter 2 Coming soon

The Trust That Protects AISH

A properly built Henson trust holds assets at the trustee's discretion, so they aren't counted against Owen's AISH. A lawyer is required.

Chapter 3 Coming soon

Taxing the Trust Gently

A Qualified Disability Trust can be taxed at graduated rates instead of the top rate. It's a layer worth professional advice from an accountant and lawyer.

Chapter 4 Coming soon

Rolling the RRSP to Owen

On a parent's death, an RRSP or RRIF can roll into Owen's RDSP, tax-deferred. Registered money lands where it keeps working for him.

Chapter 5 Coming soon

Who Gets What, On Paper

Beneficiary forms override the will. The Whitfields line up registered accounts, insurance, and the will so assets land in the trust or RDSP, not by accident.

Chapter 6 Coming soon

Insurance That Funds the Plan

Life insurance can create the lump sum the Henson trust needs, sized to Owen's lifetime. It turns a future promise into money that's actually there.

Chapter 7 Coming soon

When Owen Turns 18

Adulthood is a financial milestone too. The family plans early for Owen's own AISH and for guardianship versus supported decision-making.

Chapter 8 Coming soon

The Letter

The most important document isn't legal or financial. It's the letter of wishes that tells the next people who Owen is, what he loves, and what a good life means for him.

Chapter 9 Coming soon

A Plan That Outlives Us

The trust, the rollover, the insurance, and the letter are all in place. A complete plan lets the parents rest: Owen is secured, and so are they.

OakwiseFuture Me Is a Stranger

Retirement · Book 4

Future Me Is a Stranger

Jesse · Retirement

Expected Aug 2027

Long-horizon planning when your brain discounts the future — systems that run without daily attention, and a flexible plan for episodic income and health.

Chapter 1 Coming soon

Future Me Is a Stranger

Hyperbolic discounting makes the future self feel unreal, so long-horizon saving is uniquely hard with ADHD. Jesse names it, then lets the system carry it.

Chapter 2 Coming soon

Make the Stranger a Friend

Jesse won't always feel like saving for later, so the answer is pre-commitment: decide once, automate it, and stop relying on the mood.

Chapter 3 Coming soon

A Plan With No Homework

The best retirement plan for an inconsistent brain needs nothing most days. Jesse sets automatic long-term contributions into the RDSP and TFSA, with no monitoring.

Chapter 4 Coming soon

Good Years, Lean Years

For variable freelance pay, Jesse sets a contribution floor that always fires, then adds top-ups only when the good months come.

Chapter 5 Coming soon

When the Brain Has Lean Years Too

Episodic health can hit earning and capacity at once. Jesse builds a deeper buffer and a low-capacity default so the plan holds during the worst stretches.

Chapter 6 Coming soon

Hands Off the Long Money

Jesse puts real friction between themselves and the long-term accounts, using the RDSP 10-year holdback as built-in protection so a bad day can't undo years.

Chapter 7 Coming soon

The Money Comes Back Out

Decumulation should be as automatic as saving. Jesse designs a low-touch drawdown of RDSP payments, CPP, and OAS that a future self with less bandwidth can run.

Chapter 8 Coming soon

A Plan That Bends

Jesse stress-tests the whole plan against a bad year for both income and health, confirming it still stands and holds on autopilot.

Chapter 9 Coming soon

Still Running

The lifelong system runs itself. A money life built on systems, not willpower, keeps running long after the motivation does, and that's the relief.