The High Earner’s Guide to Intentional Spending: Finding Your Financial Middle Ground

By Ryan Goldenhar

High earners face a weird paradox. You have enough money to make serious financial mistakes, but not always enough liquidity to recover from them quickly, especially if your wealth is tied up in company stock you can’t easily access, retirement accounts you can’t touch, or real estate you can’t sell without major disruption.

Some people overspend themselves into fragility despite high incomes, while others underspend themselves into regret, missing experiences they can afford because they’re terrified of making the wrong choice.

How do you find the right middle ground?

Avoid the Comparison Trap

Keeping up with the Joneses used to mean buying a nicer lawn mower than your neighbor. Now it means a bigger house, private schools, European vacations, new cars every few years, and a lifestyle that requires every dollar you make just to maintain.

But in reality, you’re watching people’s highlight reels while missing the financial stress happening behind closed doors. Your colleague with the beach house might be overleveraged, one bad year away from having to sell. Your neighbor could be leasing their Tesla; your friends taking international trips could be financing them on credit cards.

The point is that you have no real idea what anyone else’s balance sheet actually looks like. Comparing what you have to what they appear to have will always be a losing game.

We’ve found that the subconscious ego drives most overspending. And the feeling is natural: you want visible proof that you’ve made it, which can translate into buying the bigger house, sending your kids to private school, taking expensive vacations, financing new cars every few years.

None of those choices are wrong in and of themselves. But spending for validation rather than genuine personal preference will leave you unsatisfied and in debt, not rich in joy and experience.

Plan Major Purchases Strategically

If most of your net worth sits in unvested equity, concentrated stock positions, or retirement accounts, your spending decisions become more complicated.

You might be worth $3 million on paper but only have $200,000 in accessible cash. That’s real wealth with real limitations. You can’t spend unvested RSUs or easily borrow against stock in the company where you still work. And tapping retirement accounts before 60 triggers penalties that make expensive purchases even more expensive.

Major purchases should always be planned carefully, but especially so when much of your wealth is illiquid. A $25,000 built-in refrigerator might be pocket change for someone with diversified liquid assets. For someone whose wealth is tied up in company stock, it might mean selling shares and triggering a tax event just to buy an appliance.

Some people can borrow against publicly traded stock they no longer work for, avoiding the immediate tax hit. But that only works if the company is public and you’ve already separated. While you’re still employed, your options are usually more limited.

Concentrated wealth creates spending volatility. When your company stock is up 40%, you feel empowered to spend; when it drops, you feel panicked and cut back. We believe investors should always consider keeping spending at reasonable levels regardless of what your company stock is doing. Don’t increase fixed costs based on temporary gains or start slashing subscriptions because of a drop.

Spend Where it Matters

Overspending gets all the attention, but underspending is just as damaging: you put off the family trip, keep the old car too long because a new one feels frivolous, and skip experiences your kids would love because they seem irresponsible.

Just like overspending, underspending is often a fear response. Fear of running out of money, of making the wrong choice, of what happens if you lose your job or the market takes a turn.
Some caution when it comes to spending is certainly healthy, but too much can cause you to regret missing out on what you worked so hard for in the first place.

Finding Your Middle Ground: Values-Aligned Spending

The principle is simple, but not easy: Spend money on things that matter to you. Don’t spend money on things that don’t.

It sounds like a no-brainer, but we often encounter clients who spend reflexively, based on what feels expected for people in their position. They rarely stop to ask whether what they’re buying is really improving their lives.

Start with your budget -your sustainable spending level, something you can maintain long-term without compromising your financial security or missing experiences that you’ll regret later.

Of course, this number is different for everyone and depends on a number of factors. How concentrated is your wealth? How volatile is your income? What are your fixed costs versus discretionary spending? How much liquidity do you actually have outside retirement accounts and unvested equity?

Next, take a hard look at the difference between spending for happiness and spending for validation. Spending for happiness will always be unique to you. What fulfills you? Is it travel? A comfortable home? Having the flexibility to take time off to spend with family?

Spending for validation, on the other hand, puts far more weight on what other people will think about what you’re buying than what you actually think. You can usually tell the difference by asking a single question about a purchase: “If no one knew about this, would I still want it?”

There’s no universal formula for determining your values-aligned budget, but there is a philosophy: Spend intentionally on what matters and cut back on what doesn’t. That’s what will make you financially resilient.

Keep visiting our site and follow us on LinkedIn to stay up to date with all our latest thoughts. Feel free to reach out directly if you have questions about your specific spending situation!

Frequently Asked Questions About Smart Spending

How do I know if I’m overspending?
Track your spending for three months. Then ask: if my income dropped 30% tomorrow, which expenses would I cut immediately? Those are probably things you don’t actually value. If you’re not building savings and your lifestyle requires every dollar you make, you’re overspending. If you’re stressed about money despite a high income, you’re definitely overspending.

How do I handle major purchases when my wealth is illiquid?
Define “major” for your situation. Is it $10,000? $50,000? $200,000? Once you know the number, calculate how much you’d need to sell and the tax implications. If you’re still employed and hold significant company stock, you typically can’t borrow against it. You’ll need to sell shares or save cash from income. Plan major purchases around vesting schedules when possible.

Should I borrow against my stock for large purchases?
Maybe, if you no longer work at the company and the stock is publicly traded. Borrowing can help you avoid triggering a tax event from selling. But it also adds risk. If the stock drops significantly, you might face a margin call. This is a calculation to work through with an advisor based on your specific situation and risk tolerance.

How much should I spend if my net worth is mostly concentrated stock?
Concentrated wealth is volatile wealth. Keep spending conservative until you diversify. Don’t lock in high fixed costs like a bigger mortgage, second home, or other debt-funded lifestyle inflation. Once your wealth spreads across different assets and volatility drops, you can safely increase spending.

How do I maintain stable spending when my portfolio is volatile?
Use guardrails. Set a spending floor and ceiling based on portfolio value. If your assets drop below a certain threshold, you cut spending. If they rise above another threshold, you can increase spending. The specific percentages depend on your risk tolerance and financial goals. This prevents you from dramatically overshooting in good times or panicking in bad times.

How do I figure out my “sustainable spending level”?
Start with your current spending and evaluate honestly. Which expenses improve your life? Which are just habit or social pressure? Factor in your income stability, wealth concentration, and liquidity. Account for taxes, future goals, emergency reserves. Work with an advisor to model different scenarios. Your sustainable spending level should let you enjoy life now while building security for later.

Important Disclosures:

The information provided herein is for general informational and educational purposes only and does not constitute individualized investment, tax, legal, or financial advice. The content is not intended as a recommendation to buy, sell, or hold any security, pursue any investment strategy, or take any specific employment or compensation-related action.

Examples, scenarios, ranges, and planning concepts discussed are illustrative only and should not be interpreted as indicative of typical or expected outcomes. Financial outcomes vary significantly based on individual circumstances, including income, liquidity, tax considerations, equity compensation structure, market conditions, and risk tolerance.

References to experiences or planning approaches reflect general observations and are not guarantees of future results. There is no assurance that any planning strategy, investment, or approach will be successful. Investing involves risk, including the possible loss of principal. Past performance does not guarantee future results.