What I’d Do Differently If I Were 35 With a High Income (and No Time)
If you’re 35, earning well, and constantly short on time, the biggest financial risk usually isn’t a bad stock pick.
It’s running an expensive, ad-hoc system:
cash scattered across accounts
benefits and equity comp decisions made in a rush
taxes handled after the fact
insurance and estate planning “on the list”
investments that don’t match the reality of your life (and your stress tolerance)
High income can cover a lot of mistakes… until it can’t.
Here’s what I’d do differently if I could go backwith the benefit of seeing how this plays out for busy executives and founders.
1) Build a “default” financial operating system (so you stop renegotiating decisions)
When time is scarce, you need fewer decisions, not more options.
I’d create a simple operating system that runs in the background:
One hub account for income and bills
Automated transfers on payday (investing, taxes, giving, cash reserves)
A written set of rules for big decisions (equity sales, bonuses, windfalls)
The goal isn’t perfection. It’s removing friction so you don’t have to be “on your game” every month.
2) Treat taxes like a monthly subscription, not an annual surprise
High earners often pay a “tax penalty” for being reactive.
I’d do three things early:
Run a mid-year projection (not just a year-end scramble)
Set up a tax reserve that’s separate from lifestyle cash
Coordinate comp decisions (RSUs, options, bonuses, deferred comp) with the tax plan
Most people don’t have a tax problem. They have a timing and coordination problem.
3) Assume your biggest risk is concentration (even if you feel diversified)
If you’re a SaaS exec or founder, there’s a good chance your real exposure looks like this:
a paycheck from one company
equity tied to one company
career capital tied to one industry
benefits tied to one employer
That’s not “bad.” It’s just reality.
I’d build a plan that acknowledges concentration instead of hoping it behaves.
A simple rule I like:
If one company can change your lifestyle, it deserves a written plan.
4) Create a “sell system” for equity comp before you need it
Most equity decisions are made under pressure:
stock is up and you feel greedy
stock is down and you feel stuck
blackout windows shrink your options
taxes show up at the worst time
I’d pre-commit to a system that answers:
What percentage of net worth is too much in one stock?
What triggers a trim? (time-based, price-based, or risk-based)
How will I manage taxes? (withholding, estimated payments, charitable strategies where appropriate)
This isn’t about calling tops.
It’s about turning a stressful decision into a repeatable process.
5) Keep the portfolio boringand make the risk management sophisticated
Busy high earners are the perfect target for complexity.
I’d do the opposite:
keep the core portfolio simple and transparent
use diversification intentionally (not as a buzzword)
focus on behavioral risk: what will you actually stick with?
A portfolio that’s “optimal” on paper but impossible to hold is not optimal.
6) Buy time with a real cash plan (not just a number)
Most people think of cash as a percentage.
I’d think of cash as time.
3–6 months of expenses is a start
but high earners often need a second layer: opportunity + volatility cash
Cash isn’t a return asset.
It’s a behavior asset. It keeps you from making forced decisions when life gets messy.
7) Get the unsexy stuff handled early: insurance + estate + documents
At 35, you’re often in the messy middle:
young kids
a mortgage
rising income
aging parents
equity comp complexity
I’d prioritize the basics:
term life insurance (if someone depends on your income)
disability coverage (often the biggest real risk)
umbrella liability (cheap protection)
estate documents (will, powers of attorney, guardianship)
These aren’t exciting.
They’re the foundation that keeps a bad day from becoming a permanent problem.
8) Choose your “wealth team” like you’d hire a key executive
If you’re high income and low time, the right coordination is worth more than cleverness.
I’d make sure someone is accountable for:
integrating taxes + investments + equity comp
keeping the plan updated as life changes
preventing expensive blind spots
A good team reduces cognitive load.
That’s the real ROI.
9) Set a “lifestyle ceiling” (so raises don’t disappear)
Lifestyle creep isn’t a character flaw.
It’s what happens when your spending has no rules.
I’d set a simple policy:
pick a lifestyle number that feels great
let future income increases fund goals (freedom, optionality, giving)
You don’t need to live like a monk.
You just need a plan so success doesn’t quietly become dependency.
10) Write a one-page plan you can actually follow
If your plan requires a Saturday afternoon every month, it won’t survive.
I’d keep a one-pager that answers:
what we’re optimizing for (freedom, optionality, family, impact)
the few numbers that matter (savings rate, cash runway, concentration limits)
the rules for big decisions (equity sales, bonuses, windfalls)
what happens in a drawdown (rebalance rules, no panic moves)
Clarity beats complexity.
Bottom line
At 35 with a high income and no time, the goal isn’t to “do more.”
It’s to build a system that:
makes good decisions automatic
reduces the number of high-stakes moments
protects your family and your future
and turns concentration + taxes into managed variables, not surprises
If you’re a high earner with equity comp and a busy life, a second set of eyes can help you pressure-test the systemespecially around concentration risk, taxes, and the decisions that compound over time.
