Exit & End: Crafting a New Identity Beyond Your Exit

How an exit can change your relationship with work, money, and who you are next.

For years, you’ve been working at a company approaching an exit. The day finally comes, and you receive your proceeds. You celebrate at your favorite restaurant and maybe order a couple of extra things. Then, for the first time in your career, you ask yourself a question that seems silly:

Do I actually need to keep working? What will I do now?

These two questions are more common than you think.

So, how did you get here? Maybe you took a risk on a startup and chose equity over salary. Maybe you started your own company. Maybe you joined an established company that was already close to an exit. There are so many situations, and they share an impact moment where money builds up in what feels like the snap of a finger.

It’s kind of funny. I’ve come across people who were so heads down in their careers, raising families, or simply going about their lives that they didn’t fully realize how much their financial situation was changing until it happened.

The amount looks different for everyone. When it’s enough to make you rethink your financial future, it’s enough to raise those two questions. That’s when the thoughts come storming in.

Those two questions can carry the weight of hundreds more. So let’s break them down and make them easier to digest, whether you’re going through this now or know it’s coming.

1. When Work Becomes a Choice

Most people spend their working lives making decisions with financial considerations at the center. What does the job pay? How much can I save? Can I afford to take a career risk? Am I putting enough away for retirement?

For those in the startup space, there’s another layer. You’ve spent years accepting concentrated equity exposure, uncertain liquidity timelines, and the possibility that the equity could be worth zero.

A successful exit or liquidity event can change that equation. Suddenly, you may have options that weren’t financially realistic six months ago:

• Retire earlier: Maybe the original plan was to work until 60, but now retiring at 50 is possible.
• Change careers: Take a lower-paying role in an industry or profession that genuinely interests you.
• Spend more time with family: Reduce your hours, take an extended break, or allow your spouse to step away from work.
• Continue working: Stay in a career you enjoy, knowing that your financial future no longer depends entirely on your paycheck.
• Take 6+ months off: Step away from work to travel, pursue hobbies, work on personal projects, or simply see how you enjoy having a different routine.

Here’s the hard truth… For years, your job gave you more than income. It gave you structure, a team, and a one-breath answer to “what do you do?” When the paycheck stops being the reason you show up, those things don’t disappear on their own, and they don’t automatically get replaced either. Part of planning your next phase of life is deciding what you want to carry forward and what you want to build new.

One thing I’ve come to appreciate is how important it is to have parts of your life that have nothing to do with your profession. I genuinely enjoy being a financial advisor, but I also love spending time with my wife, getting out on the golf course, traveling around the world, and being involved in organizations that are meaningful to me.

Those parts of my life don’t depend on what I earn or what my job title says. When I think about financial independence, I think about having more control over how much time I can dedicate to all of those things.

A few questions worth asking that weren’t part of your career planning before:

• If compensation were no longer the deciding factor, would I still want my current job? If the answer is no, what would I want to do?
• Would I enjoy working fewer hours or taking on fewer responsibilities?
• Do I actually want to retire, or do I just want more control over my schedule?

There’s no right answer. Some people love their careers and have no interest in slowing down. Others realize they’ve spent years working toward financial independence without giving much thought to what they’d do once they achieved it. Financial independence doesn’t necessarily mean you have to retire. For some people, it simply means being able to say no to opportunities they don’t want and yes to ones they previously couldn’t afford to pursue.

Just because you don’t need to work doesn’t mean you won’t want to.

2. Don’t Rush Into Your Next Big Decision

You’ve potentially just experienced the largest financial event of your life. It’s exciting, and there’s naturally going to be some temptation to make changes.

Maybe it’s quitting your job, purchasing a vacation property, or investing in new companies. None of those decisions are necessarily wrong, but I’d encourage anyone going through a major exit to understand their financial position before making permanent commitments.

I’ve spent a lot of time on the golf course, both playing and caddying for hundreds of golfers. One thing I’ve learned is that not every situation calls for an aggressive shot. Sometimes going for it is the right decision. Other times, laying up puts you in a much better position.

I think there’s a similar lesson after a liquidity event. You’ve already taken significant financial risk by having so much of your wealth tied to one company. Before taking another big swing, it’s worth understanding what you’re potentially putting at risk.

Consider this hypothetical, for illustration only. Someone who is 42 years old receives $4 million after taxes from an acquisition. That’s a life-changing amount of money, but whether it’s enough to retire permanently depends on several factors:

• Annual spending: A family spending $120,000 annually has very different needs from one spending $300,000.
• Time horizon: Someone retiring at 42 might need their portfolio to support 50 or more years of expenses.
• Future obligations: Children’s education, healthcare, housing, and family support can meaningfully affect long-term projections.
• Investment risk: Markets won’t deliver consistent returns every year, especially over a retirement that could span several decades.
• Remaining compensation: Unvested equity, retention bonuses, employee benefits, and other compensation may be affected by leaving your employer.

Before submitting your resignation or making a substantial purchase, run the numbers. Build a financial plan that accounts for multiple market environments, inflation, taxes, and changing spending needs.

The goal isn’t to discourage you from making changes. It’s to understand how much flexibility you actually have and to feel confident about this next phase of life.

3. Figure Out What Your “Enough” Number Looks Like

One of the most important questions I think someone should ask after a liquidity event is:

What amount of money would permanently change my family’s financial life if I protected it?

AKA your number. You’ve probably heard this before. Seriously though, what’s your number?

It’s different for everyone. For one family, having the mortgage paid off, their children’s education funded, and enough invested to support their lifestyle might be all they need. Another family might have significantly more wealth but also greater financial obligations.

Let’s say you’ve received $6 million in after-tax proceeds. Through comprehensive financial planning, you determine that $4.5 million, combined with your existing assets, could potentially support your family’s long-term financial goals under a range of assumptions.

You could begin separating your wealth into different priorities:

• Long-term financial security: A diversified investment portfolio designed to support future spending, retirement, and other major obligations.
• Near-term lifestyle needs: Cash reserves and funds for anticipated purchases, travel, or other expenses.
• Future opportunities: Capital earmarked for another startup, angel investments, or other ventures where you can afford to accept additional risk.
• Family and legacy: Education funding, charitable giving, estate planning, or helping family members.

These aren’t necessarily separate investment accounts, and the numbers aren’t a universal formula. The important part is assigning a purpose to your wealth so you’re not treating every dollar the same way.

Once you understand what you need to protect, it becomes much easier to determine what you can afford to pursue.

4. Enjoy Your Money Without Accidentally Recreating Financial Pressure

If you’ve spent years accumulating startup equity and suddenly have several million dollars available, you’re probably going to want to enjoy some of it. I’m all for that!

I think it’s incredibly important to take a moment to appreciate what it took to get here. The years of hard work, the risks you took, the sacrifices you made, and the sweat equity you put in along the way.

One thing my wife and I really value is traveling and experiencing new places together. We recently took a trip to Tanzania and Kenya for a safari, and it’s an experience we’ll remember for the rest of our lives.

It was something we intentionally prioritized because those memories and experiences are important to us. I bring that up because I think money is meant to be enjoyed, too. We spend so much time talking about saving, investing, and growing our wealth that sometimes we forget why we’re doing it in the first place.

For you, maybe that means upgrading your home, taking more vacations, helping your parents financially, or paying for your children’s education. Those are meaningful benefits of financial success, and there’s nothing wrong with enjoying the outcome of years of hard work.

The one thing I’d caution against is allowing every part of your lifestyle to expand at once. A few common examples:

• A larger home: Beyond the purchase price, you’re committing to higher property taxes, maintenance, insurance, and other recurring expenses.
• A vacation property: It might create great family memories, but it also introduces ongoing costs and additional responsibilities.
• Private education: Paying for multiple children through high school or college can create substantial future spending obligations.
• Investment opportunities: Angel investments and private businesses can tie up capital for years, with no guarantee of getting it back.

Individually, these decisions might be completely affordable. Collectively, they can change your financial independence number considerably. For example, using the popular 4% annual withdrawal rate, an additional $100,000 in recurring annual spending would require roughly $2.5 million more in invested assets. That’s an illustration, not a guaranteed sustainable withdrawal rate, especially for someone retiring early.

Your actual number will depend on your age, spending needs, taxes, investment strategy, and retirement timeline. That’s why it’s worth modeling instead of guessing.

It’s also important to evaluate lifestyle decisions together rather than one at a time.

The goal isn’t to avoid spending money. It’s to avoid unintentionally creating a lifestyle that requires you to keep earning at the same level you did before your exit.

The Bottom Line

For startup employees, a successful liquidity event can represent the financial reward for years of patience, hard work, and taking a chance on a company.

The real value of that event isn’t necessarily the size of the payout. It’s what the money makes possible.

You’ve spent years making career decisions that helped build your wealth. Now you have the opportunity to make decisions about how that wealth can support your life.

Remember that question that seemed silly at the start? It isn’t. It’s the beginning of a conversation worth having.