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Ready For Retirement

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

Ready For Retirement

James Conole, CFP®

Investment Planning, Bonds, Education, Stocks, Cash, Business, Dividend Investing, Retirement Planning, Retirement, Investing, Tax Planning

5706 Ratings

🗓️ 22 April 2025

⏱️ 18 minutes

🧾️ Download transcript

Summary

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 har...

Transcript

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0:00.0

Are you worried about taking the tax hit on your investment gains and unsure what to do?

0:03.7

Well, in today's episode, I'm going to share a very simple framework that will show you when,

0:07.6

or even if, you should realize those gains and the way you should go about doing it.

0:13.7

This is another episode of Ready for Retirement.

0:16.2

I'm your host, James Cannell, and I'm here to teach you how to get the most of the life with your money.

0:20.5

And now, on to the episode.

0:24.0

As part of this episode, I'm going to share with you simple ways that you can pay nothing in taxes

0:27.9

on some of these gains. This is from simple things, like taking full advantage of the

0:31.3

0% long-term capital gain tax bracket, creative ways to gift money to charity to offset

0:36.5

the tax impact, gifting money to children

0:39.0

so they can realize some of the gains at their tax bracket, understanding when you get a step

0:42.3

up on your unrealized gains, and also understanding how tax loss harvesting can help to offset

0:47.1

some of this. So I'll talk about some of those, but before I do so, I want to go through the general

0:50.8

framework of how you should even think about the gains that you have in your portfolio.

0:55.1

You've invested in something that's grown, and now you're stuck wondering, what do I do?

0:59.1

Do I take the tax hit?

1:00.6

Or do I keep it going to avoid taxes and maintain the same investment exposure that I already have?

1:05.8

And just in case it's not already obvious, what I'm talking about specifically is gains in a brokerage account.

1:10.3

Not an IRA, a Roth IRA, a 401k. All of those gains are either tax-free or tax-deferred.

1:16.5

I am talking about gains on things held in a brokerage account where anything that you realize,

1:20.9

any gain that you realize, is potentially subject to taxes. So to start, let's go through the

1:25.2

framework of when should you hold onto your investment and avoid paying gains versus when should you sell your investment and pay taxes on those gains.

...

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