Winding Trail Financial Blog

Retirement, tax, & financial planning articles and insights

Grandfather celebrating with grandson on college acceptance

Trump Account vs. 529 Plan: Which Is Better for Your Child or Grandchild?

Illustration of a Social Security card with a low fuel gauge, symbolizing questions about whether Social Security is running out of money.

Is Social Security Really Running Out of Money? What Retirees Should Know

Medicare IRMAA and Retirement Tax Planning

What Colorado Retirees Should Know About Medicare IRMAA and Tax Planning

Couple considering long-term care planning

What If I Never Use Long-Term Care Insurance?

Retiree investingating grocery bill amidst inflation

The Silent Retirement Risk: Why Inflation Can Be More Dangerous Than Market Volatility

Colorado teacher retirement planning

Colorado PERA Retirement Planning: 5 Things to Know Before You Retire

Grandparents hugging their grandson while considering savings options like Trump Accounts and 529 plans

What Are Trump Accounts? A Guide for Grandparents and Families

For in the road in the San Juan Mountains

What Should You Do With a Concentrated Stock Position Before Retirement?

Wankea Lake in Lafayette Colorado near the Office Headquarters

Should You Pay Off Your Mortgage Before Retiring in Colorado?

Retired couple reviewing financial documents at the kitchen table

What Taxes Will Retirees Pay in Colorado?

Retirement tax surprise

The truth about how much Retirement Benefits are taxed

Boulder Foothills Near Lafaytte CO Office

Tax-Smart Retirement Withdrawals for Boulder County Retirees

Plan Your Next Chapter

Download our free guide "Seven Essentials for Successful Investing in Retirement" and get clarity on what really matters for your retirement success.

Preparing for Retirement Guide

Plan Your Next Chapter

Download our free guide "Seven Essentials for Successful Investing in Retirement" and get clarity on what really matters for your retirement success.

Preparing for Retirement Guide

Plan Your Next Chapter

Download our free guide "Seven Essentials for Successful Investing in Retirement" and get clarity on what really matters for your retirement success.

Preparing for Retirement Guide