The Jackson Group at CIBC Wood Gundy

The Jackson Group at CIBC Wood Gundy Jennifer Jackson leads The Jackson Group at CIBC Wood Gundy, focusing on the needs of late-career professionals facing early retirement options.

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I've had some version of this conversation with nearly every client. "We'll do the big trip once things slow down." And ...
09/09/2026

I've had some version of this conversation with nearly every client. "We'll do the big trip once things slow down." And I understand the instinct completely.

But a destination like the Swiss Alps asks something of you physically. The glacial lakes, the alpine meadows, the trails that go just a little further past the cable car. Those experiences belong to the years when your body is still on board.

That's not a reason to worry. It's a reason to plan on purpose.

The clients who build a trip like this into their working years, or into the early years of retirement, tend to look back on it as one of the best-timed decisions they ever made. Not the biggest. The best-timed.

One of our newest team members, Ben Cook, just came back from Switzerland and Oeschinensee was very much a hike, not a drive-up viewpoint. He's twenty-two and did it now because he could.

The same logic applies at every age.

If Switzerland or any active bucket-list destination is sitting on your someday list, it might be worth asking whether someday should actually be sooner.

Read the full post here: https://bit.ly/4A40MRK

09/06/2026

In this week’s Week Ahead, Avery Shenfeld notes that the US and Japan are facing a common challenge: rising long-term bond yields and tighter fiscal constraints. With slower growth and higher borrowing costs, managing government debt may become much harder.

08/30/2026

In this week’s Week Ahead, Avery Shenfeld makes the case that, even after last week’s breakdown in trade talks, Canada still needs to stay at the table with the U.S.

While reducing that dependence is an important long-term goal, his view is that the immediate priority is to keep dialogue open and work with U.S. allies who also have a stake in avoiding further escalation.

A conversation I have more often than you'd think...A couple sits across from me. They've saved diligently for 35 years....
08/28/2026

A conversation I have more often than you'd think...

A couple sits across from me. They've saved diligently for 35 years. Their plan is solid. Their retirement is fully funded. Then one of them says, almost apologetically: "We were thinking about business class for the flight to Portugal… but it seems like a lot."

They can comfortably afford it. And they're asking permission.

Nobody warns you that the hardest part of retirement planning isn't saving the money, it's giving yourself permission to spend it. After decades as a "saver," watching the balance go down (on purpose, on schedule!) feels wrong.

My latest article is about the risk we never talk about: reaching 85 with more money than you retired with, and a list of things you never did.

Read the full article here: https://bit.ly/4xrmwVW

08/23/2026

In this week’s Week Ahead, Avery Shenfeld argues that the U.S. midterms are unlikely to materially alter trade policy, given that much of the Trump agenda has been advanced through executive orders.

This helps explain why Canada has not seen the post-midterm period as a particularly promising window for tariff negotiations.

08/16/2026

In this week’s Week Ahead, Avery Shenfeld notes that despite the recent calm in markets, the outlook for the Persian Gulf and oil prices remains highly uncertain.

He argues that the current stability in crude should not be taken as reassurance, since prices could move lower if a deal is reached, or rise sharply if the standoff persists.

"When should I take my CPP?"It might be the question I hear most often from clients approaching retirement usually asked...
08/14/2026

"When should I take my CPP?"

It might be the question I hear most often from clients approaching retirement usually asked in a slightly guilty whisper, as if everyone else already knows the answer.

Here's the truth: the math is the easy part. Delaying from 65 to 70 increases your benefit 42%, guaranteed and indexed for life. On paper, waiting often wins.

But a spreadsheet can't weigh your health, your family history, your pension bridge, your tax picture as a couple or what you want your 60s to actually look like.

In my latest article the four questions the CPP calculator can't answer. Here: https://bit.ly/45XlDsa

08/09/2026

In this week’s Week Ahead, Avery Shenfield highlights the surprising rebound in Canada’s export sector, with real export volumes reaching a new high in Q2 and helping support GDP growth.

While energy and some US-bound exports have led the recovery, ongoing tariff risks, weak manufacturing investment, and capacity constraints suggest the momentum may be difficult to sustain.

The cottage is rarely the largest asset in a family's estate plan. But it's almost always the hardest one.It's where the...
08/07/2026

The cottage is rarely the largest asset in a family's estate plan. But it's almost always the hardest one.

It's where the kids learned to swim. Where three generations fit around one picnic table. Which is exactly why the questions "who gets it, who pays for it, what's fair" keep getting kicked down the road.

Here's what I tell cottage families... the conversation is only awkward once, avoiding it can be painful for a generation.

My latest article covers the human questions to ask first, the tax bill nobody budgets for (including one piece of genuinely good news on capital gains), and why this summer is the time to start.

Link to the full article here: https://bit.ly/4w9MXyd

08/02/2026

In this week’s The Week Ahead, Avery Shenfeld examines what the bond market may be signaling about the Fed’s decision to hold rates steady, and unpacks one of the key unanswered questions from Chair Warsh’s press conference on inflation, growth and the likelihood of further rate hikes.

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