When is the Best Time to Realize Gains in my Investment Account?

If you’re sitting on large investment gains in a brokerage account and wondering whether it’s worth taking the tax hit, this episode is for you. I walk through a clear framework I use with clients to help them decide when—and if—it makes sense to realize those gains.

I also explain several strategies that can potentially reduce or even eliminate the taxes you might owe, including how to take advantage of the 0% long-term capital gains tax bracket, gifting appreciated assets, and tax-loss harvesting. Whether you're approaching retirement or just looking to be more intentional with your investments, these tools can help you make more informed decisions.

Toward the end, I also point to a related video where I explain how a separately managed account may benefit high-income investors with significant brokerage assets.

Questions answered:
1. When does it make sense to realize investment gains in a taxable brokerage account—and when should you hold off?

2. What strategies can help reduce or eliminate the taxes owed on long-term capital gains?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - When not to sell
2:40 - Understand risks on both sides
5:54 - Tax strategies
8:55 - Gifting stocks to charities
11:14 - Gifting to family
12:44 - Understanding step-up in basis
14:18 - Capital losses offset capital gains
15:11 - Wrap-up

Create Your Custom Strategy ⬇️

Get Started Here.

Join the new Root Collective HERE!