Tag: tax planning

Roth Conversions Can Save You A Lot in Taxes Over Your Life. What’s the Best Way to Do Them?

Block Woman surveys three pastel colored buckets: blue, red and green. The green bucket is balanced on top of the red bucket and is tilted against Block Woman.

A Roth conversion can potentially save you a lot of money over your lifetime. It is a long-term (years or decades-long) strategy, to be sure. It is one that is usually talked about in the context of retirees.

How We Evaluate and (Hopefully) Improve a Client’s Existing Portfolio

Block Woman looks at a jumbled pile of multi-colored puzzle pieces.

As much as I think most of investing is boring (and should be), I really enjoy the puzzle of what to do when I first start working with a client’s existing investment portfolio. And how I work through that puzzle might help you evaluate and improve your own investment portfolio.

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Our Investment Beliefs

A black-and-white image of Block Woman perched on a rough-hewn rock. Block Woman appears to be contemplating their shadow.

I rarely talk about investing in this blog. It has been on purpose.

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Employee Stock Purchase Plans (ESPP): Enroll, But Don’t Get Too Excited.

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Do you know, more or less, how RSUs work, but ESPPs are a complete mystery? Join many of our clients in that confusion. And frankly they are stupidly complicated for the amount of money they’re worth to you.

And while Employee Stock Purchase Plans are fairly common in big public tech companies, they’re not nearly as common as RSUs. Google and Amazon, for example, have RSUs but not ESPPs.

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Should You Exercise Your Options at Your Private Company? 4 Approaches to Consider

Block Woman balancing on a slender tightrope in the top third of the image.

This is for all you private-company employees out there who still have your job. And have exercisable stock options hanging over your head, causing persistent low-key anxiety about:

Should I be doing something with these?

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Your 401(k) Match Can Now Be Roth (and Other Changes from the SECURE 2.0 Act)

Block Woman looking at a wall with the word "Roth" written many times on it.

Congress passed the Secure 2.0 Act in late 2022. Why should you care? You shouldn’t. Much.

401(k) legislation retirement savings tax planning taxes

Avoid These 5 Big Tax Mistakes with RSUs, Stock Options, and ESPP

Block Woman is wearing a battered tan-colored wool hat. There are 3 traps nearby: a cement block; a lasso; a green jungle camouflage.

Stock compensation can be a great pathway to wealth, but they also come with their own set of tax implications. Unfortunately, many taxpayers miss important tax considerations when it comes to stock compensation.

espp RSUs stock options tax planning taxes

Has your tax season sucked? Make some changes now to make next year better (suck less).

If your tax season sucked (stressed out, last-minute activity, uncertainty, unexpectedly big tax payments), then, while the pain is still fresh, let’s think about how to make your life way less stressful next year.

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You Can Save in Three Different Tax “Buckets.” What Are They, and Why Should You Care?

I’m violating one of the cardinal rules of content marketing here by writing about something I want you to know about, instead of something that you want you to know about.

retirement savings tax planning taxable vs. retirement savings

How Could the House and Biden Tax Proposals Affect You? What Should You Do Before Year’s End?

Have you been hearing a lot about the tax proposals coming out of Washington D.C.? First it was President Biden’s back in April. In early September, it was the House Ways and Means Committee’s. And currently, as of the time of publishing, the tax proposal situation in Congress is anybody’s guess.

tax planning taxes

Should I withhold 22% or 37% on my RSUs when my company goes public?

As so many of my blog posts seem to, this one starts with “Congratulations! Your company is going IPO! Now you have…all these decisions to make.”

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What Women in Tech Need to Know about the Recent Stimulus Package

As you might be aware, in late December 2020, the president signed into law another round of economic stimulus. In March 2020, we had the CARES Act. Now we have the Consolidated Appropriations Act of 2021.

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