For business owners and families with net worth exceeding $5 million, tax season is more than filing returns — it’s one of the most important planning windows of the year.
By February, the numbers are clearer: corporate income, capital gains, dividends, and personal tax exposure are coming into focus. This makes now the ideal time to step back and assess a much bigger question:
Is your estate plan structured to minimize tax — not just this year, but over your lifetime and at death?
For many high-net-worth families, the largest tax bill is not paid while living, but when an estate is settled. Without proper planning, capital gains tax, probate costs, and administrative expenses can significantly reduce what ultimately passes to family.
Why February Matters
Tax time brings clarity. It highlights:
February is often when gaps become visible — and when proactive planning can still make a meaningful difference.
Key Estate & Tax Planning Considerations for Business Owners
Corporate & Holding Company Planning
If a significant portion of your wealth is held corporately, your estate may face substantial capital gains tax at death. Strategies such as estate freezes, share reorganizations, and trust planning can help cap tax exposure and shift future growth to the next generation in a controlled way.
Succession & Family Transition
Transferring a business to children or future leaders without tax-aware planning can trigger unintended consequences. Effective succession planning considers timing, valuation, control, and tax efficiency — not just who takes over.
Trust & Income Planning
While income-splitting rules have changed, trusts can still play a critical role in managing growth,
protecting assets, and planning for future generations when structured correctly.
Planning for Capital Gains on Death
Without planning, unrealized gains are triggered at death. Insurance strategies, charitable planning, and trust structures can be used to fund or reduce this liability, preserving more wealth for heirs.
Coordination Matters
Tax strategies must align with your Wills, shareholder agreements, and powers of attorney. When
these pieces are disconnected, opportunities are lost and risk increases.
Estate Planning Is Strategic — Not Just Legal
A common misconception is that estate planning is simply about documents. For high-net-worth families, it is a strategic process that integrates tax planning, trusts, business succession, asset protection, and family governance.
Tax season is when the financial picture is clearest — and when reviewing your estate plan is most effective.
Join Us: Complimentary Webinar — February 26 at 6:30 PM
To explore these topics in more detail, MacMillan Estate Planning is hosting a complimentary estate planning webinar focused on tax planning, business owners, and high-net-worth families.
Date: Wednesday, February 26
Time: 6:30 PM (MT)
Format: Live webinar
Register here:
https://www.macmillanestate.com/seminars
This session is designed for business owners and families who want to proactively minimize tax, plan for succession, and protect their legacy — before opportunities are missed.