Life's biggest decisions
The decisions all happen before you resign
Most of what a job change costs or saves is decided in the two weeks before you give notice, not in the two months after.
Why now
Why this moment is different
For most of your career, compensation arrives and you decide what to do with it afterward. A job change inverts that. The value of what you already hold depends on choices you make in a narrow window, and several of those choices cannot be revisited.
Unvested equity is usually the largest number in the conversation and the one people look at last. Acceleration provisions differ widely between plans, so two colleagues leaving the same company in the same month can have very different outcomes. Vested options carry their own clock: leaving typically starts a limited post-termination exercise window, commonly ninety days, though your plan document is what governs.
Deferred compensation is the quiet one. Distribution triggers were set when you made the election, often years ago, and separation from service is frequently one of them. That can land a large distribution in the same tax year as a severance payment and a final bonus, which is a bracket problem nobody chose.
Then there is the new offer, which arrives as a headline number. Comparing it honestly means pricing the equity you are walking away from, the vesting cliff you are restarting, and the benefits that reset.
What goes wrong
The mistakes we see most often
Reading the plan documents after giving notice
Acceleration, forfeiture, and exercise windows are all in documents you can request while you are still employed. Once notice is given, the terms are simply the terms.
Letting the deferred comp election run on its default
Separation is often a distribution trigger. If nobody checks, a deferred balance can arrive in the same year as severance and a final bonus, taxed together.
Comparing offers on base salary
The number that matters is total compensation after the equity you forfeit, the cliff you restart, and the tax treatment of each piece. Two offers with the same base are rarely the same offer.
Treating the exercise window as a formality
A post-termination window on vested options forces a decision that combines cash, taxes, and concentration risk, usually within weeks and usually while starting a new job.
Leaving old employer plans behind
A 401(k) at each former employer means an allocation nobody set on purpose. Consolidating is sometimes right and sometimes not, but it should be a decision rather than an oversight.
Assuming the timing is fixed
A start date a few weeks either side of a vest date, a bonus payment, or a year end can change the tax year everything lands in. Sometimes that is negotiable.
How we help
What we do with you
We build one page that shows what you hold and what happens to each piece if you leave: every grant with its vest schedule and acceleration terms, your deferred comp distribution triggers, your severance language translated into monthly cash flow, and the tax year each item would land in.
Then we look at sequence. Which decisions have hard deadlines, which have room, and whether moving your start date by a few weeks changes the tax outcome enough to be worth raising in the negotiation.
If an offer is on the table, we price it against what you are leaving rather than against your current base. That comparison is usually the part people have not been able to do on their own, because it needs the equity detail and the tax picture in the same view.
The work behind it
What this usually touches
- What this involves →
Executive compensation
Deferral elections, bonus timing, benefit choices, severance terms. Each one is a decision, and most of them default if you leave them alone.
- What this involves →
Equity compensation
Vest dates arrive whether or not anyone has thought about them. The work is deciding, ahead of time, what you sell, what you hold, and what the tax bill will be.
- What this involves →
Tax strategy
Most tax advice assumes you own a business. When your income is a paycheck, the levers are fewer, and using them depends entirely on timing.
- What this involves →
Retirement income
It is the question most people ask late and quietly. Answering it properly takes an afternoon, and the answer changes how you feel about the next ten years.
Who this usually is
How this starts
Three steps, and the first one costs you an hour
Step 01
Tell us your story
About an hour, no cost, no obligation to do anything afterward.
- How you got to this point, in your own words. Career, family, the decisions that shaped the last ten years.
- What keeps your attention at odd hours. Usually it is more specific than money in general.
- What success looks like to you. Not a number we hand you, the version you would describe to a friend.
- Who is already in your corner: your CPA, your attorney, anyone else we should be working alongside.
Straight about money
The first meeting is free
If we go ahead together, planning carries a fee, and you will know the number before you commit to anything. For households above $1 million in assets we manage, it is typically waived.
Straight answers
Changing jobs: common questions
That is the right time. Almost everything worth deciding here is decided before notice: what you can request from your plan administrator, whether a start date is negotiable, and whether it is worth waiting for a vest date. After notice, the same conversation becomes a matter of working out what the documents already say.
In most plans, unvested awards are forfeited on separation, with exceptions written into the plan for retirement eligibility, a change in control, or a negotiated agreement. Because those exceptions vary widely and usually carry the largest dollar figure in the decision, this is the first thing we read rather than the last.
By pricing both in the same terms. Staying is worth the retention award plus continued vesting, adjusted for the risk that the role changes. The package is worth the severance plus whatever accelerates, landing in a specific tax year. Once both are in cash-flow terms, the decision is usually clearer than it feels.
It depends on the investment options and costs in each, whether you want the option of a Roth conversion later, and in some cases on creditor protection rules that differ between plan types. Sometimes leaving it is the better answer. What matters is that it is a decision someone made deliberately.
This material is for general educational purposes only and is not intended as tax, legal, or investment advice. Neither GGM Wealth Advisors nor Cambridge provides tax or legal advice. Please consult a qualified professional about your specific situation.
Let's start with a conversation
Bring whatever is on your mind: a vest date you are unsure about, an offer you are weighing, a business you might sell in three years. Nothing to prepare, no cost, and you will leave with something useful whether or not we end up working together.