Introduction

This is NOT Financial Advice

In the theme of giving up value for simplification, I’ve decided in 2026 to not frontload all my investing in the beginning of the year. I have three main reasons that made me reconsider this strategy.

Temptations

I’ve noticed that I feel the temptation to fiddle with my portfolio even though I know objectively it’s a waste of time and that I just have to wait to get most of the gains. So I thought if I give up frontloading, I can set up my automations one time before the year starts and then reduce the number of interactions with my accounts. The only manual tasks I have left are for the Employee Stock Purchase Plan (ESPP) and Restricted Stock Units (RSUs) because my company turned off the ability to automatically sell them. I’ve created a default playbook where I will save 10 percent of any RSUs or ESPP payout as savings, allocate 2-3 months of the Roth IRA of the following year, and then invest the rest in a taxable brokerage account. If I set 15% Pre-Tax 401k, 20% Post Tax 401k (In Plan Conversion), and a fixed amount in my taxable brokerage, I should be able to still max out every account. I need to do a quick check in January because the order that everything is deducted (even for After Tax) can be confusing.

Edit

Because ESPP is such a pain to deal with I’ve decided to frontload the traditional 401k. I set these percentages so I don’t need to change anything for the whole year

• Traditional 401k - 65%
• After Tax Conversion - 15%
• ESPP - Kept maxed out

Savings

I would like to bolster my savings a bit more in 2026. I think the author Morgan Housel gave a fantastic way to think about how much cash savings to have. Right when you think you have a little bit too much savings is the perfect amount. And that for me is about a year’s worth of savings. By not frontloading I’m more consistently saving for every category I need. One thing that has already happened in frontloading is that I forget to fund certain savings goals because before I only saved manually after cashing out RSUs or ESPP payouts.

Thoughtful Spending

This one is one I didn’t expect but I feel more compelled to actually spend money on things with “fresh” money from my paycheck. For example I feel like I would actually spend 500 dollars on eating out per month if I got the money that month vs trying to spend 1/3rd of 1500 dollars dedicated to 3 months of eating out. Objectively they are the same but looking at my YNAB history, I can tell the way I behave in the first half of the year and the second half of the year is completely different. I want to force myself to spend a fixed amount of money on something I want. For now it’s trying new restaurants in Seattle.

Inefficiencies and Risks I Accept

The most obvious risk is if I get laid off I will not be able to get the 401k match and looking for new jobs right now is probably horrible. One potential upside is that my 401k match actually tapers off so they give you more for your first 10K or so and then half for the rest. So If I do find a job with a half decent match, I can potentially get a better deal if I can find a job in the second half of the year.

The two main inefficiencies are getting the 401k match all upfront and funding the ESPP late. Getting the 401k match upfront just means that I get basically 1.5X the number of shares earlier which I can hold inside an account where I will not pay taxes for dividends. Generally it’s better to hold shares for a longer amount of time. If you’re holding for multiple decades, doing this frontloading is generally advantageous.

Because I have to pay into ESPP every paycheck but I don’t get anything in return until the sale time twice a year, it’s better to buy index funds over paying for ESPP early. By frontloading I could actually have a bunch of 0 dollar paychecks and delay paying into ESPP until the very end. ESPP in my company is locked in for the year once you sign up so it’s not like the 401k where you can change the percentage contribution at any time.

Conclusion

I think in the long run the changes I’m making are more sustainable and prevent me from sabotaging myself. I think this will be the last financial post in a while. I’m sure at some point I will have to do a job change or I get laid off and I’ll do an update after that happens.