Go Back to All Articles

Jan 28, 2026

Why the Last 10 Years Should Change How You Plan for the Next 10

If you’ve seen the 2016 vs. 2026 trend floating around Instagram, you’ve probably noticed a common theme.

Different clothes.

Different careers.

Different cities.

Different priorities.

At first glance, it feels like lighthearted nostalgia. But underneath the trend is a much deeper and more important insight, one that has major implications for how we think about money, planning, and the future.

The End of History Illusion

In 2013, a group of Harvard researchers studied more than 19,000 people and asked two simple questions:

  • How much have your values, preferences, personality, and priorities changed in the last 10 years?
  • How much do you expect them to change in the next 10 years?

Across every age group, from teenagers to people in their late 60s, the results were remarkably consistent.

People believed they had changed a lot in the past, but expected to change very little in the future.

The researchers called this tendency the End of History Illusion, the belief that who you are today is essentially who you’ll always be.

The last 10 years show just how unreliable that assumption can be, especially financially.

  • $100 in 2016 has the same buying power as $136.78 today
  • $100 invested in the S&P 500 in 2016 would be worth $261.06 today
  • Compensation structures, tax rules, work flexibility, and career paths have all shifted dramatically

And yet, many financial plans are still built as if the next decade will be predictable.

________________________________________

Change Shows Up as the Questions People Actually Ask

How do we know when change is happening, when the plan we once had or the version of ourselves it was built for no longer quite fits?

It usually shows up as questions typed into Google or asked quietly to a trusted advisor.

For high-earning, dual-career couples, especially those with stock compensation, businesses, or demanding professions, these are some of the conversations we have most often.

1. Stock Compensation Requires Ongoing Decisions, Not One-Time Ones

In 2016, stock compensation often felt like a bonus.

In 2026, for many professionals, it is the compensation.

RSUs, options, and equity awards introduce decisions that cannot be put on autopilot:

  • Sell versus hold decisions
  • Managing concentration risk
  • Timing sales for tax efficiency
  • Coordinating vesting with cash flow and life goals

What worked when equity made up 10 percent of income often breaks down when it grows to 40 to 60 percent.

Stock compensation is not just an investment decision. It is a planning decision that needs regular attention as your income, risk tolerance, and priorities evolve.

2. Retirement Planning Is No Longer a Binary Question

The old model was simple:

Work → retire at 65 → stop earning.

That model does not reflect how many high-earning households actually live today.

Instead, we often see:

  • One spouse slowing down before the other
  • Sabbaticals or career pivots
  • Business exits instead of traditional retirement
  • Periods of high income followed by intentional breaks

Rather than asking “When do we retire?”, better questions tend to be:

  • When do we want more flexibility?
  • How soon do we want access to invested assets?
  • Are we saving in the right types of accounts for an uncertain timeline?

This is where tax-diversified savings, pre-tax, Roth, and taxable, become essential, not optional.

3. Tax Strategy Must Evolve as Income Evolves

In 2016, many households focused primarily on marginal tax rates.

In 2026, effective tax planning is far more dynamic and often includes:

  • Coordinating RSU sales with deductions or charitable giving
  • Strategic Roth conversions in lower-income years
  • Business-owner retirement plans
  • Planning when income shows up, not just how much

Tax strategy is not a one-time decision. It evolves as income becomes more complex and as life changes.

________________________________________

A good financial plan evolves when those questions do, not years later.

Planning for the Next 10 Years Means Planning for Change

The last decade brought:

  • A global pandemic
  • Historically low and then rapidly rising interest rates
  • Massive shifts in work, location flexibility, and compensation
  • Tax law changes that reshaped planning strategies

Very little of this was broadly anticipated in 2016.

As Pliny the Elder put it:

“The only certainty is that nothing is certain.”

Market volatility gets the headlines. But for complex households, the bigger risk is planning for a version of yourself that will not exist in 10 years.

At Vitality Wealth, we believe the goal is not predicting the future. It is building a plan that can adapt as your life evolves.

In practice, that looks like…

  • Designing cash flow and savings systems that flex with changing income
  • Stress-testing plans against multiple future scenarios
  • Treating equity compensation and concentrated assets intentionally
  • Revisiting assumptions regularly, not just portfolios
  • Aligning money with values that will evolve, not just the ones you hold today

The 2016 vs. 2026 trend is a reminder of how much can change in a decade. The next 10 years will likely surprise us too. The question is not whether you will change, but whether your financial plan is built to change with you.

That’s where we come in. If you want a financial plan built to adapt as your life, income, and priorities change, we’d love to start the conversation.
Click here for a free consultation.

Jessica Smith, CFP® CPA