This week's issue
Why down years in sales are sometimes the best tax planning years you'll have.
4 min read
Who this is for
This newsletter is built specifically for sales reps.
Not general advice for anyone who works. This is for people whose income actually moves -- big commission years, soft years, OTE that swings depending on quota and market.
If that's your situation, every issue of Intentional Finance is written with you specifically in mind. The tax decisions, the investment moves, the planning frameworks -- all of it is designed around variable income.
If that's not you, a lot of what we cover won't apply the same way. And that's fine -- this just isn't the newsletter for you.
Sound like you? This comes out every week. It's free.
Join FreeThis week's take
"Roth is always better." You've seen this take. It's on every finance account, every YouTube channel, every LinkedIn post that gets 10,000 likes.
The people saying it aren't lying. Roth is powerful. But "always better" isn't financial advice. It's content strategy. Simple takes go viral. Nuance doesn't.
Traditional contributions can be incredibly powerful, especially in the right year. And traditional money that you convert to Roth at the right time can be even more powerful. The question isn't which is better. It's which is right for you, this year.
The Decision Should Follow Your Income
Most sales reps pick one and stick with it. Roth or traditional. Set it and forget it.
The problem is that your income isn't flat. Some years you hit $300K. Some years you have a soft patch and land at $140K. Those are two completely different tax situations, and they call for two different decisions.
When you're deep in a high bracket, traditional contributions reduce your taxable income right now -- when the tax hit is highest. A $23,500 traditional 401(k) contribution in a $280K income year could save you $6,000+ in federal taxes today.
That's real money. Don't give it away just because someone on the internet said Roth is always better.
Here's the reframe most people miss. When your income drops, so does your tax bracket.
That's a planning opportunity.
If you have pre-tax money sitting in an IRA or an old 401(k), a down year is often the best time to convert some of it to Roth. You pay taxes at a lower rate. The money grows tax-free from there. Future withdrawals are tax-free.
Down years feel like a step back. In tax planning terms, they're often a green light.
Tax Planning for Sales Reps
The Down Year Window
| YEAR 1 | YEAR 2 | DOWN YEAR | YEAR 4 | YEAR 5 |
| $260K | $295K | $130K | $240K | $310K |
| 32% bracket | 35% bracket | 22% bracket | 32% bracket | 37% bracket |
| Traditional | Traditional | Convert to Roth | Traditional | Traditional |
| Lower income = lower bracket = cheaper Roth conversion | ||||
Some sales reps aren't clearly in one camp or the other. You're probably here if:
When you're riding the ridge, the answer is usually a split. Traditional for the dollars that land in the higher bracket. Roth for the rest. Conversions in softer years to keep things moving in the right direction.
Roth vs. Traditional
Riding the Ridge
| TRADITIONAL | THE RIDGE | ROTH |
|
High-income year $250K+ income 32% or 35% bracket Expect lower income in retirement Need to reduce taxable income now |
Split + convert Income swings year to year Unclear retirement bracket Mix of both account types Convert in down years, save in high years |
Down year Under $150K income 22% or 24% bracket Expect higher income later Time to convert old pre-tax accounts |
Traditional money isn't a permanent decision.
You can convert pre-tax IRA money to Roth strategically -- a little at a time, in lower-income years. This is called a Roth conversion, and it's one of the most underused tools in a sales rep's financial plan.
And if your income is too high to contribute directly to a Roth IRA, there's the backdoor Roth -- a two-step process that works around the income limits entirely.
Tax Planning for Sales Reps
The Income Spectrum
| ROTH ZONE | GRAY ZONE | TRADITIONAL ZONE |
| Under $120K | $120K -- $220K | $220K+ |
The people telling you "always Roth" are simplifying for a reason. Simplicity goes viral.
But you're not trying to go viral. You're trying to build wealth.
Every week, Intentional Finance covers exactly this -- the financial decisions that matter to sales reps with variable income. Not generic advice. Not content written for everyone.
If your income swings year to year and you want a clear framework for making smart decisions with it, this is where that lives.
It's free. New issue every week.
Join Intentional Finance - FreeBefore you keep reading
Intentional Finance is a free weekly newsletter built specifically for sales reps whose income swings year to year. Every issue is written for that exact situation.
If your paycheck doesn't move much, this newsletter will still make sense -- it just won't hit as directly. But if you're running on commission and OTE, this was made for you.
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