The Retirement Checklist: Setting Yourself Up for Your Golden Years

Retirement sounds simple. Stop working. Enjoy life. Travel. Relax.

The reality is much more complex. Especially for high-net-worth individuals.

You’ve built significant wealth. Multiple income streams. Global investments. Business interests. Real estate holdings. Your financial life has many moving parts.

Retirement doesn’t mean these disappear. It means managing them differently.

Planning 10 to 15 years ahead gives you time to optimize. Time to fix problems. Time to build the retirement you actually want.

This checklist covers the essential steps. Follow it and your golden years will be truly golden.

Calculate Your Real Number

Most retirement calculators are useless for wealthy individuals.

They assume you’ll live on 70% of your current income. They don’t account for multiple properties, philanthropic goals, or supporting adult children. They ignore business transitions and complex assets.

You need a real calculation.

Start with lifestyle costs. What does your current life cost annually? Include everything. Properties. Travel. Staff. Hobbies. Healthcare. Don’t guess. Track actual spending for a year.

Add future goals. Want a vacation home? Plan to increase travel? Support grandchildren’s education? These aren’t extras. They’re part of your retirement vision.

Account for inflation. A comfortable $500,000 annual lifestyle today costs $820,000 in 20 years at 3% inflation. Your calculation must reflect this.

Plan for longevity. You might live to 95 or beyond. Medical advances extend lifespans. Plan for 30 years of retirement, not 20.

Include healthcare costs. These rise faster than general inflation. Even with good insurance, expect significant out-of-pocket expenses as you age.

Factor in support for others. Many wealthy individuals support family members. Adult children. Aging parents. Charitable commitments. Include these obligations.

Once you have this total, multiply by 30 years. That’s your baseline target. Your investment portfolio needs to generate this amount while preserving capital.

Restructure Your Investment Portfolio

Your working years portfolio focused on growth. Your retirement portfolio needs balance.

Shift toward income generation. Dividend-paying stocks. Bonds. Real estate income. You need cash flow to cover expenses without constantly selling assets.

Reduce concentration risk. Many wealthy individuals have fortunes tied to one business or sector. Diversify before retirement. Concentrated positions create unnecessary stress.

Create a cash reserve. Keep 2-3 years of expenses in liquid, safe assets. This prevents forced selling during market downturns.

Adjust risk gradually. Don’t dump all stocks at retirement. But reduce equity exposure over time. A 60/40 or 50/50 stock-bond mix often works for retirees.

Consider alternative investments. Private equity. Hedge funds. Real assets. These can provide diversification and returns uncorrelated with public markets.

Plan withdrawal strategy. Which accounts do you tap first? Taxable accounts? Tax-deferred? Tax-free? Withdrawal order affects how long money lasts.

Review portfolio allocation annually with advisors. Market changes and personal circumstances require adjustments.

Plan Your Business Exit

Your business might be your largest asset. Transitioning it requires careful planning.

Decide on succession or sale. Will the family take over? Key employees? Or will you sell to outsiders? Each path requires different preparation.

Begin transition early. Successful transitions take 5 to 10 years. Rushing creates problems and destroys value.

Build management depth. The business can’t depend entirely on you. Develop strong leaders who can run operations independently.

Get proper valuation. Know what your business is worth. Professional valuation reveals true value and areas needing improvement.

Address tax implications. Business sales trigger major tax events. Proper structuring can save millions. Work with specialized tax advisors.

Create liquidity for estate taxes. If heirs inherit the business, they’ll face estate taxes. Life insurance or other funding prevents forced sales.

Define and document institutional knowledge. Your relationships, processes, and insights have value. Transfer this knowledge systematically.

A successful business transition preserves both financial value and your legacy.

Optimize Estate Planning

Your estate plan needs updating as retirement approaches.

Review and update documents. Wills. Trusts. Powers of attorney. Documents from 10 years ago don’t reflect current laws or circumstances.

Minimize estate taxes legally. Gifting strategies. Trust structures. Charitable vehicles. Proper planning can save 30% to 50% in taxes.

Clarify asset distribution. Who gets what? Be specific to prevent family conflicts. Ambiguity creates fighting.

Address digital assets. Cryptocurrency. Online accounts. Digital businesses. These need specific provisions in estate plans.

Plan for incapacity. Healthcare and financial powers of attorney. Living wills. These matter before death.

Consider dynasty trusts. For multi-generational wealth preservation. These protect assets for grandchildren and beyond.

Coordinate beneficiary designations. Retirement accounts. Life insurance. These pass outside wills. Make sure designations match your overall plan.

Meet with estate attorneys every 2-3 years. Laws change. Your family changes. Plans must adapt.

Find and Define Your Purpose

Money isn’t enough for fulfilling retirement. You need purpose.

Identify meaningful activities. What will you do with your time? Hobbies alone don’t sustain most people long-term.

Consider phased retirement. Full stop often feels jarring. Many executives transition gradually through board positions, consulting, or part-time roles.

Explore philanthropic goals. Giving back provides deep satisfaction. Establish foundations. Support causes you care about. Create lasting impact.

Plan for relationships. Retirement changes family dynamics. Spouses suddenly spend all day together. Be intentional about maintaining healthy relationships.

Stay intellectually engaged. Learning doesn’t stop at retirement. Take courses. Read deeply. Engage with ideas.

Maintain social connections. Work provides social structure. Replace it deliberately. Join clubs. Volunteer. Stay connected to communities.

Consider location carefully. Where will you live? Near family? In a favorite climate? Proximity to quality healthcare? Location affects retirement satisfaction significantly.

Purpose planning matters as much as financial planning. Start thinking about this now.

Review and Adjust Regularly

Retirement planning isn’t one-time. It’s ongoing.

Schedule annual reviews with your advisory team. Check progress toward goals. Adjust for market changes, law changes, and life changes.

Update calculations as you get closer. More precise numbers become possible as retirement nears.

Communicate plans with family. Surprises create problems. Transparency builds understanding and alignment.

Stay flexible. Life rarely follows plans exactly. Build a cushion for unexpected events.

Conclusion

Retirement planning for wealthy individuals involves more than saving money. Business transitions. Complex investments. Estate optimization. Healthcare preparation. Purpose definition. All of these require attention.

Starting 10 to 15 years ahead gives you time to handle each element properly. Rush and mistakes happen. Plan deliberately and retirement becomes what you want it to be.

Your golden years should be exactly that. Golden. Not stressful. Not uncertain. Not chaotic.

Proper planning makes this possible.

The Xanara Edge

At Xanara, we help high-net-worth families navigate complex retirement transitions. Our comprehensive wealth management approach addresses all aspects of retirement planning, from investment restructuring to estate optimization to purpose planning. We coordinate with your existing advisors to ensure nothing falls through the cracks. Your retirement deserves the same careful attention you gave to building your wealth.