You’ve made it.
Not in the performative sense - not the LinkedIn highlights or the dinners where people measure themselves in job titles. But in the real sense. The version where you’ve built something that works. Created value. Built trust. Led people. Delivered results. Provided for your family. Crossed the threshold most never reach.
And now, whether you admit it or not, you’re thinking about what comes next.
But instead of feeling clear, you find yourself circling the same quiet questions:
What happens when I’m not needed the same way?
What will my days actually look like when I’m no longer driving the business?
Will the next chapter feel like a reward - or like being sidelined?
These aren’t dramatic questions. They don’t keep you up at night. But they linger. They show up in small moments: when someone asks about your “retirement plans,” or when your adult children ask about the family business. When a colleague your age has a health scare. Or when you’re staring at a spreadsheet and realize… the numbers aren’t the hard part anymore.
You’re not looking for someone to sell you a product. You’re looking for someone to help you make sense of the next chapter.
That’s where this begins.
To everyone else, you look like a success story. You’ve created wealth. Led people. Navigated risk. Maybe even exited a business.
But you know that the next decisions - the ones ahead of you now - carry a different kind of weight.
There’s no roadmap for stepping away from relevance. No manual for handing off the company you spent decades building. No script for how to support your children without accidentally disempowering them. And no one tells you what it feels like when the adrenaline slows down.
Retirement planning for founders isn’t about stopping. It’s about navigating the emotional complexity of letting go while staying grounded in who you are.
What’s coming next isn’t a problem to be solved. It’s a future to be shaped - carefully, thoughtfully, and on your terms.
Most of the founders and senior executives I work with don’t come to me because of a crisis. They come because the success they’ve built is now too important to leave unstructured. And they’ve realized they don’t want to guess their way through the next decade.
They say things like:
“I’ve spent my life creating stability. I don’t want to accidentally blow it up by getting this part wrong.”
“I don’t want to be in the business forever, but I also don’t want to just walk away.”
“I can afford to give my kids a lot. I’m not sure if I should.”
“I’ve built wealth. I want to use it wisely - but I’m not sure what that looks like now.”
Underneath it all is one theme: they want to remain in control - of their time, their values, and their impact - without feeling like they’ve let go of their identity.
This isn’t just about tax efficiency. It’s about legacy, clarity, and peace of mind.
At this stage, more ideas aren’t helpful. You’ve got enough whitepapers and suggestions floating around. What you need is structure — the kind that simplifies without dumbing down.
You might be wondering:
These are high-quality problems. But that doesn’t make them easy. And without clarity, complexity creates drag. People stall. Money sits idle. Teams drift. Families wait for direction that never fully arrives.
It doesn’t have to be that way.
Here’s the truth: even the most capable people need a sounding board. Especially when the stakes are personal.
That’s the role I play.
Not as the star. Not as a guru. But as a trusted, quiet voice in the background - helping you think clearly, weigh trade-offs, and build the structure that lets you move forward with confidence.
I work with founders, international executives, and entrepreneurial families who’ve outgrown simplistic planning. They’re looking for clarity, structure, and a way to design their lives with intention - across borders, business holdings, and generations.
We start with your goals, but not in the usual “growth target” sense. We begin with what matters to you. Not the company. Not the spreadsheet. You.
Because this next chapter? It’s not about performance. It’s about presence.
There’s no one-size-fits-all. But there is a rhythm to the process that helps people move from tension to clarity.
We start with your story. What’s changed? What’s coming? What’s unclear? The best retirement planning for expats, business owners, and senior executives always begins with the person, not the portfolio.
We map what matters - not just net worth, but cash flow, risk exposure, ownership structures, family goals, relocation plans, and timelines. This includes scenario modeling for events like: selling your business, supporting family members, moving countries, or starting a new venture.
Once we have clarity, we build the financial architecture to match it. That may include succession planning, retirement income modeling, offshore trust structures, strategic gifting, or preparing for a liquidity event. We align everything so your decisions aren’t reacting to problems - they’re driving your vision forward.
There’s no noise. No pressure. Just calm, focused work that brings order to complexity and turns uncertainty into options.
Even when people know they need a plan, they hesitate. Here’s what I hear most often:
“I’m not ready to retire.”
You don’t need to be. Planning is about creating freedom, not forcing a finish line. Making work optional doesn’t mean walking away - it means
knowing you could and feeling good either way.
“It feels indulgent to spend time on this when there’s still work to do.”
You’ve already created value for others. This work is about protecting it, extending it, and making sure it continues to serve you and your family. That’s not indulgent - it’s responsible.
“I’ll get to it when the business is further along.”
By the time people say this, they’re already past the point where planning would be most powerful. Whether it’s transferring equity, preparing a successor, or simplifying cross-border finances - the earlier you build structure, the more options you keep.
“My situation is too complicated for a clean solution.”
That’s exactly why you need someone who’s used to complexity. Most of my clients don’t have cookie-cutter lives. That’s the point.
Let’s name what this work actually is. It’s not about retirement in the traditional sense. You’re not shutting down.
It’s about readiness.
Financial planning for executives approaching retirement doesn’t mean planning to disappear. It means planning to live --with structure, with control, and without avoidable stress.
Most people at your level don’t fear losing money. What they fear is losing relevance, purpose, or control.
You’re not worried about being “done.” But you are asking what it means to move into a new phase without slipping into uncertainty. You’re asking:
What does it mean to step back when work has defined me - but I no longer want it to own me?
How do I create a life where I have full choice - and no regrets?
That’s the work.
And that’s where we’ll go next - into the structure, principles, and mindset that allow you to design a future that feels solid, meaningful, and genuinely optional.
Not because you need to stop. But because you deserve to choose.
What does it mean to step back when work has defined me - but I no longer want it to own me?
This is where many high-level founders and international executives find themselves. The business has matured. The pressure is still there, but it’s changed. And for the first time in years - maybe ever - you’re thinking ahead not just as a builder, but as a steward.
There’s no panic. Just a subtle pull: the desire to be intentional with what comes next.
This isn’t about financial freedom in the startup sense. This is about clarity. About building a life where work is truly optional - not just technically, but emotionally. Where you’re not grinding out of habit or fear, but choosing with your eyes open.
So, let’s get specific. Because staying vague is what keeps smart people stuck.
Let’s redefine retirement.
For someone who’s run companies, created wealth, and lived internationally, “retirement” rarely means a hard stop. You’re not interested in playing golf five days a week or downsizing into irrelevance.
What you want is control over your time. Space to pursue what interests you. The freedom to travel without checking Slack. The ability to support your family without wondering if it’s “too soon.” The confidence that your business or wealth won’t collapse if you step away.
That’s what real retirement planning for expats and founders looks like. It’s not about locking money away in a pension. It’s about creating structure so your income, ownership, risk, and responsibilities evolve as you evolve.
You can call it retirement. You can call it succession. Or you can just call it a new chapter. The label doesn’t matter. What matters is that it works for your life.
Too many plans obsess over net worth. That number feels good on paper, but it doesn’t tell you what you can actually do.
Planning based on assets without understanding cash flow is like planning a road trip by only looking at the size of your fuel tank.
Instead, ask:
A global executive might have:
Each source carries its own risks, opportunities, and tax treatments. Cash flow modeling should reflect your lifestyle plans - not just your accountant’s year-end report.
If you want to make work optional, the first question isn’t can you stop working? It’s how would you fund your life if you did?
You can hire lawyers to draft the documents. You can set up structures to manage risk. But you can’t outsource the thinking that matters most.
Legacy doesn’t mean dropping a lump sum into a trust and hoping for the best. It means asking:
Succession planning for founders is not just about company equity. It’s about preparing people. Whether you’re handing the business to a child, selling to a third party, or building a family office, the transfer of understanding matters more than the transfer of ownership.
Good planning turns uncertainty into conversation. It takes the weight of guesswork off your shoulders and helps your family avoid the tension that so often creeps in when plans are left unspoken.
If your life crosses borders, so does your complexity.
Planning isn’t just about having enough. It’s about access, timing, control, and taxation - across jurisdictions.
Here’s what that might include:
Making work optional requires a structure that doesn’t fall apart when you stop actively managing every detail. You need systems that let you own the outcome without constantly manning the controls.
Let’s look at three real scenarios - the kinds of situations I see again and again.
A founder in his early 60s wants to sell his company in stages over the next five years. His goal is to exit cleanly but keep strategic influence. He also wants to help two adult children buy property, without creating entitlement.
His questions:
The solution involved a staged sale with a holding company in a tax-efficient jurisdiction, gifting through a trust with oversight provisions, and personal cash flow planning so he could explore a second career without financial pressure.
A 55-year-old former C-suite executive is splitting time between Europe, Southeast Asia, and the U.S. She has equity from several past roles, rental properties in two countries, and a large inheritance expected within ten years.
Her questions:
The solution involved modeling tax scenarios across three jurisdictions, aligning her residency with a country offering favorable treatment, and preparing her structures to receive future wealth cleanly.
A couple in their early 60s have grown wealth through multiple ventures and now want to focus on family and impact. They’re considering $3M in gifts to their children, and a further $2M in impact investments.
Their questions:
The plan included a family governance framework, gifting through an offshore trust with clear stipulations, income modeling to ensure financial resilience, and selecting impact investments aligned with their values that still produced retirement-level returns.
The clients I work with aren’t confused. They’re capable. They’ve been the decision-maker for decades. What they’re looking for now isn’t more control - it’s smart release.
To let go of the things that no longer serve them.
To delegate what should no longer be theirs to carry.
To move into this next chapter with the same clarity they brought to the first one.
Retirement planning for expats, succession planning for founders, legacy structuring - these are just labels. The real work is in giving yourself the freedom to live with intention, without carrying unnecessary friction.
That freedom starts with structure. And structure starts with the decision to stop doing it all in your head.
You’ve carried enough responsibility. You’ve earned the right to step into a chapter where your calendar reflects your values, your wealth reflects your priorities, and your family isn’t left guessing.
You don’t need to race. You don’t need to retreat. You just need to move forward with clarity.
The planning that matters now isn’t about squeezing more returns out of your portfolio. It’s about shaping a life you actually want to live - with the confidence that you’ve taken care of what matters, and the space to enjoy it.
Work optional. Values intact. Legacy protected. On your terms.
That’s the point.
Retirement planning for expats involves structuring your income, assets, and tax exposure across multiple countries. It includes decisions about residency, access to funds, healthcare, and estate planning in jurisdictions that may not align. If you plan to live, retire, or invest abroad, your retirement plan must reflect those international realities - not just domestic assumptions.
Making work optional means building the financial and structural clarity to walk away - or stay involved - without pressure. For many founders and executives, it’s not about stopping work. It’s about gaining the freedom to choose what they do, when, and for whom. That requires cash flow planning, simplified ownership structures, and a clear understanding of what “enough” looks like.
Succession planning for founders goes beyond choosing a replacement. It involves preparing the business, the people, and the ownership structure for transition. That can include staged exits, equity restructuring, tax planning, and conversations with family or key team members. The goal is continuity - both financial and cultural - without sacrificing control too early or too late.
Executives nearing retirement often have deferred compensation, international assets, and complex benefit plans. Their financial planning needs to coordinate income timing, tax location, and long-term security. Unlike early-career professionals, this stage is about preservation, control, and strategic transition - not just accumulation.
Yes - but it depends on how it’s done. Structured giving through trusts or staged distributions can protect your capital, offer tax efficiency, and give your children support without creating dependency. Effective legacy planning balances generosity with responsibility, especially when large amounts are involved.
There’s no single answer. Many expats choose to retire abroad for lifestyle, tax, or cost-of-living reasons. Others return home to be closer to family. The key is planning early for healthcare, currency risk, tax treatment, and estate exposure. A well-designed retirement plan for expats considers both options and keeps them open.
Sources:
If you’ve already ‘made it’ - and now want to make it count - we should talk.
We work with a maximum of 12 new families, executives, or founders each year to simplify complexity, and organise our client intake quarterly. Our minimum retainer fee is $2,400 per annum.