Markets rarely move in a straight line.

Some years feel calm and predictable. Other years feel chaotic. Interest rates change, inflation shifts, elections create uncertainty, geopolitical events affect sentiment, and investors are constantly exposed to headlines suggesting that the next major market move is just around the corner.

During uncertain periods, many investors ask the same question:

Should I move to cash and wait for a better time to invest?

It is a fair question. No one wants to invest right before a market decline. No one wants to watch their portfolio fall. And no one wants to feel like they missed an obvious warning sign.

But the problem is that successful market timing requires getting two decisions right:

• When to get out
• When to get back in

Getting one of those decisions right is hard. Getting both right consistently is even harder.

For most long-term investors, the better question is not, “Can I perfectly time the market?”

The better question is:

 How do I build a portfolio and financial plan that allow me to stay invested through uncertainty?

What Does it Mean to “Time the Market”?

Timing the market means trying to buy and sell investments based on predictions about short-term market movements.

An investor may move to cash because they believe markets are about to fall. They may delay investing because they believe a better entry point is coming. They may sell after a strong rally because they believe markets have gone too far. Or they may wait for “clarity” before putting money to work.

In theory, this sounds logical. Sell before markets decline. Buy before markets recover.

In practice, it is extremely difficult.

Markets are forward-looking. By the time news feels obvious, prices may already reflect it. Markets can rise during bad economic news and fall during good economic news. Investor sentiment can shift quickly. And some of the strongest market days often occur close to some of the most stressful periods.

This is why market timing can be so damaging. The investor may avoid some downside, but they may also miss the recovery.

What Does “Time in the Market” Mean? 

Time in the market is the idea that long-term wealth creation is usually driven by staying invested through full market cycles rather than trying to move in and out perfectly.

This does not mean doing nothing.

It does not mean ignoring risk.

It does not mean blindly buying and holding every investment forever.

It means building a portfolio that is aligned with your goals, your time horizon, your liquidity needs, your tax position, and your tolerance for volatility – then allowing that plan enough time to work.

A disciplined long-term investor understands that volatility is part of the process. Market declines are uncomfortable, but they are not unusual. The key is to avoid letting short-term fear derail a long-term plan.

Why Timing the Market is so Tempting

Market timing is tempting because it offers emotional relief.

When markets are falling, cash feels safe. Selling can create a sense of control. Waiting can feel prudent. And in the short term, avoiding volatility may feel like a win.

The challenge is that emotional comfort and good investment outcomes are not always the same thing.

Moving to cash may reduce short-term stress, but it creates new problems:

• When do you reinvest?
• What if markets recover before you feel comfortable?
• What if you wait for a correction that never comes?
• What if inflation erodes your purchasing power?
• What if sitting in cash delays your retirement goals?
• What if tax consequences are triggered by selling?
• What if your portfolio is no longer aligned with your financial plan?

For investors with significant wealth, the decision is rarely just about market direction. It also affects taxes, retirement income, estate planning, corporate assets, and long-term compounding.

The Real Cost of Waiting for Certainty

Investors often say they want to wait until there is more certainty.

The issue is that markets usually recover before certainty returns.

By the time the economy looks healthy, headlines are positive, interest rates feel predictable, and investor confidence has improved, markets may already be materially higher.

Long-term investors are rarely rewarded for waiting until everything feels safe.

That does not mean you should invest recklessly. It means your investment decisions should be guided by a plan, not by the emotional tone of the headlines.

Certainty is not an investment strategy.

When Holding Cash Does Make Sense

This article is not an argument against cash.

Cash plays an important role in a well-built financial plan.

Cash may be appropriate for:

• Emergency reserves
• Upcoming tax payments
• Short-term spending needs
• Major purchases
• Retirement income reserves
• Business liquidity
• Corporate working capital
• Opportunistic investment flexibility
• Reducing portfolio volatility

The problem is not holding cash. The problem is holding excess cash with no defined purpose.

For example, a retiree drawing income may need a cash reserve to avoid selling investments during a market decline. A business owner may need liquidity inside the corporation for tax payments, payroll, or future opportunities. A family planning a home purchase should not expose that money to unnecessary market risk.

But cash intended for long-term growth has a different job. If that capital is sitting idle for years because the investor is waiting for a perfect entry point, it may create a drag on long-term wealth creation.

The Difference Between Market Timing and Disciplined Rebalancing

It is important to separate market timing from disciplined portfolio management.

Market timing is usually reactive. It is often driven by fear, predictions, headlines, or short-term market views.

Disciplined rebalancing is different.

Rebalancing means adjusting the portfolio back toward its intended allocation. If equities rise significantly, a portfolio may become too aggressive and require trimming. If equities fall significantly, a portfolio may become too conservative and require adding. This is not guessing. It is process-driven risk management.

A disciplined portfolio process may include:

• Reviewing asset allocation
• Rebalancing periodically
• Harvesting gains or losses where appropriate
• Managing cash needs
• Adjusting risk as retirement approaches
• Reviewing tax consequences before trades
• Reducing concentration risk
• Updating the investment policy as life changes

This is very different from moving everything to cash because of a headline.

Why This Matters More for High-Net-Worth Investors

For high-net-worth families, executives, and business owners, investment decisions are often more complex.

A simple “buy or sell” decision may affect:

• Personal taxable accounts
• Corporate investment accounts
• Holding companies
• Trusts
• Retirement income planning
• Capital gains tax
• Estate liquidity
• Insurance planning
• Business succession planning
• Charitable giving
• Foreign assets or cross-border considerations

That is why investment decisions should not be made in isolation.

For example, selling a large non-registered position may reduce market exposure, but it could also trigger a taxable capital gain. Holding too much cash inside a corporation may feel safe, but it may also reduce long-term compounding or create missed planning opportunities. Taking too much risk near retirement may create sequence-of-return risk, while taking too little risk too early may create inflation risk.

The right answer depends on the full picture.

The Behavioural Side of Investing

One of the most overlooked parts of wealth management is behaviour.

Investors do not usually make poor decisions because they are unintelligent. They make poor decisions because markets are emotional.

Fear can push investors to sell at the wrong time. Greed can push investors to take too much risk after markets have already risen. Recency bias can make recent events feel more important than long-term evidence. Loss aversion can make short-term declines feel more painful than equivalent gains feel rewarding.

A strong investment process helps protect against those instincts.

It creates structure before emotion takes over.

Instead of asking, “What do I feel like doing today?” the investor can ask:

• What does the plan say?
• Has my time horizon changed?
• Has my need for liquidity changed?
• Has my risk tolerance changed?
• Has the purpose of this money changed?
• Is this decision improving the plan or reacting to fear?

That shift matters.

A Simple Case Study: Sitting on Cash During Uncertainty

Consider a business owner who sold part of a business and now has a significant amount of cash.

They are nervous about investing because markets feel expensive, interest rates are uncertain, and economic headlines are mixed. They decide to wait until things feel clearer.

Six months pass. Then twelve months. The cash is still sitting there.

At first, this felt prudent. But now there are new questions:

• How much cash is actually needed for taxes?
• How much should remain liquid?
• How much should be invested over time?
• Should the money be invested personally or corporately?
• Should the portfolio be built all at once or in stages?
• What is the long-term objective of the capital?
• How does this affect retirement, estate, and tax planning?

A structured plan may divide the capital into different buckets.

• One portion may remain in cash for taxes and liquidity.
• One portion may be invested gradually.
• One portion may be used to create retirement income.
• One portion may be used for estate or insurance planning.
• One portion may be allocated to alternative investments if suitable.

This approach avoids the all-or-nothing decision.

The client is no longer trying to perfectly time the market. They are building a strategy around purpose, timeline, and risk.

A Better Framework for Investing During Uncertain Markets

Instead of trying to predict the next move, use a planning framework.

1. Identify the purpose of the money

Is this money for retirement in 20 years? A home purchase in two years? Corporate liquidity? Tax payments? Estate planning? Income needs? The purpose determines the risk level.

2. Separate short-term money from long-term money

Money needed soon should generally be treated conservatively. Money intended for long-term growth may need to remain invested to preserve purchasing power and compound over time.

3. Review your asset allocation

A portfolio should reflect your goals and risk tolerance. If the portfolio is too aggressive, reduce risk thoughtfully. If it is too conservative, understand the long-term cost.

4. Use staged investing where appropriate

For investors nervous about investing a lump sum, a staged approach can help. This may involve investing over several months instead of all at once. It does not guarantee better returns, but it can reduce emotional pressure.

5. Rebalance instead of reacting

Use volatility as a reason to review the portfolio, not abandon the plan.

6. Consider tax before trading

Selling investments can create tax consequences. Before making major changes, review the after-tax impact.

7. Connect investment decisions to the financial plan

The portfolio is only one piece. It should connect to cash flow, retirement planning, corporate planning, estate planning, and risk management.

Common Mistakes to Avoid

1. Waiting for the perfect entry point

There is rarely a perfect entry point. Markets often move before investors feel comfortable.

2. Moving entirely to cash because of headlines

Headlines may create urgency, but they do not always create good investment signals.

3. Confusing activity with strategy

Making frequent changes may feel productive, but it can increase costs, taxes, and behavioural mistakes.

4. Ignoring taxes

The decision to sell should be evaluated after tax, especially in non-registered and corporate accounts.

5. Taking too much risk because markets have been strong

Strong markets can make investors overconfident. Risk management matters most when investors feel least worried.

6. Taking too little risk because markets feel uncertain

Being too conservative can also be risky if the portfolio no longer supports retirement, inflation protection, or long-term growth.

How Evergreen Wealth Management Helps

At Evergreen Wealth Management, we help clients make investment decisions within the context of a broader financial plan.

That means we do not view market volatility in isolation. We consider how each decision affects:

• Portfolio construction
• Risk management
• Retirement income
• Tax efficiency
• Corporate investment accounts
• Cash flow needs
• Estate planning
• Liquidity
• Behavioural discipline
• Long-term family wealth

For business owners, executives, retirees, and high-net-worth families, the goal is not to guess every market move correctly. The goal is to build a plan that can withstand uncertainty and still move toward the desired outcome. 

One Final Thought

There will always be a reason to wait.

There will always be uncertainty. There will always be headlines. There will always be someone predicting the next correction, recession, rally, or crisis.

The most successful investors are not usually the ones who perfectly predict every turning point. They are the ones who build a disciplined plan, stay aligned with their goals, manage risk thoughtfully, and avoid letting emotion control long-term decisions.

Timing the market may sound appealing.

But for many long-term investors, time in the market – supported by proper planning, diversification, tax awareness, and risk management – is often the more reliable path. 

How Evergreen Wealth Management Helps

At Evergreen Wealth Management, we help clients make investment decisions within the context of a broader financial plan.

That means we do not view market volatility in isolation. We consider how each decision affects:

• Portfolio construction
• Risk management
• Retirement income
• Tax efficiency
• Corporate investment accounts
• Cash flow needs
• Estate planning
• Liquidity
• Behavioural discipline
• Long-term family wealth

For business owners, executives, retirees, and high-net-worth families, the goal is not to guess every market move correctly. The goal is to build a plan that can withstand uncertainty and still move toward the desired outcome.

Worried About Whether Your Portfolio is Positioned Properly?

Evergreen Wealth Management helps business owners, executives, retirees, and families build investment strategies designed around their full financial picture – not just short-term market headlines.

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This information has been prepared by James Hogan who is an Investment Advisor/Portfolio Manager for iA Private Wealth Inc. and does not necessarily reflect the opinion of iA Private Wealth. The information contained in this newsletter comes from sources we believe reliable, but we cannot guarantee its accuracy or reliability. The opinions expressed are based on an analysis and interpretation dating from the date of publication and are subject to change without notice. Furthermore, they do not constitute an offer or solicitation to buy or sell any of the securities mentioned. The information contained herein may not apply to all types of investors. The Investment Advisor/Portfolio Manager can open accounts only in the provinces in which they are registered.

iA Private Wealth Inc. is a member of the Canadian Investor Protection Fund and the Investment Industry Regulatory Organization of Canada. iA Private Wealth is a trademark and business name under which iA Private Wealth Inc. operates.