What Financial Steps Might Tech Professionals Take in October?

Photo of Kevin Estes smiling and wearing a dark suit with a black tee shirt. Behind him is an out of focus wooden background.

Hello, I’m Kevin - a financial planner who helps tech professionals and their families live great lives.

Make yourself at home - we'll get to potential October steps in a moment.

But first - here are some links you may want to save for later.

Is It Worth Holding Employer Stock?

Pros and Cons of a Health Savings Account

Schedule Your PTO ASAP

Now, let's get on to the blog! 😀

Title: "October" with bullet points: Evaluate stock purchased at a discount, Book holiday plans, Complete open enrollment, Update beneficiaries and estate plan, and Plan year and health expenses. Wooden background, leaves and Scaled Finance logo.

It’s Fall!

The days are getting shorter. Pumpkin spice lattes are flowing. High schools are playing football. Fall is here. 🍁

However, we still have a quarter of the year left. Let’s finish strong!

Potential Steps for Tech Professionals This Month

Financial steps tech employees might take in October include:

  1. Evaluate stock purchased at a discount

  2. Book holiday plans

  3. Complete open enrollment

  4. Update beneficiaries and estate plan

  5. Plan year end health expenses

1. Evaluate Stock Purchased at a Discount

Tech employees may have just purchased company stock at a discount. It’s worth considering what to do with those shares. 🤔

How Employee Stock Purchase Plans Work

Some plans take 15% off the lower of:

  • the beginning and

  • end of each six-month offering period.

Even if the stock fell over the six months, it may have been purchased at a 15% discount. 👏

Impact of Selling Right Away

If someone sells right away, they might realize about an 18% return! 🎉

Realized gains would be taxed as ordinary income at the employee’s marginal tax rate. However, an employee may not want - or be able - to sell immediately.

May Buy Fewer Shares

Qualified ESPP contributions are limited to the lower of:

  • 15% of qualifying compensation or

  • $25,000 each year.

That’s a federal rule so please don’t complain to your supervisor, HR business partner, or CFO about it! 😉 The same goes for the 15% discount.

Someone who contributed the full 15% and earned at least $166,667 for the year (including bonus) likely hit the $25,000 cap.

For more, check out:

How Does an ESPP Work?

Are Employee Stock Purchase Plans Underrated?

Own Stock or Contribute to ESPP?

New RSU Vest

Many employees just had some stock vest! Those shares might fund a cash reserve.

For more, check out:

Is It Worth Holding Employer Stock?

What to Do With RSUs?

How Are RSUs Taxed?

2. Book Holiday Plans

Now is a great time to book holiday flights and lodging:

  • Vacation rentals tend to book.

  • Flights prices start to rise.

  • Calendars get full.

It’s not just the calendars of friends and family. You need to consider your coworkers’ as well!

Scheduling Paid Time Off (PTO) early is like calling dibs on days off. 🎀

Avoid the drama. 🎭 Schedule your holidays now.

3. Complete Open Enrollment

Open enrollment is just around the corner!

Now’s a good time to plan for 2026:

  • Will your family have large medical expenses that might be better served by a lower deductible healthcare plan? 🏥

  • Is your youngest child turning 13, ending dependent care Flexible Spending Account (FSA) reimbursements?

  • Do you need more, less, or about the amount of life and disability insurance?

You can start planning even before the benefits guide is released!

For more, check out:

How Disability Insurance Works!

Pros and Cons of a Health Savings Account

4. Update Beneficiaries and Estate Plan

Could there be a better time to check your beneficiaries than around Halloween? 🎃

Doing so is critical because account titling and beneficiary designations almost always take priority over a last will & testament!

Is Your Estate Plan Up to Date?

Has anything changed since the last time you updated your estate plan?

  • Welcomed a new family member? 👶🐕

  • Lost a family member or close friend?

  • Relocated to a new state?

  • Bought a property?

  • Grown your net worth?

Each of these can have major implications if something happens to you.

Will You Owe Estate Taxes?

The estate exclusion for federal taxes is $13.99 million. It’s scheduled to rise further to $15 million in 2026.

However, some states have a much lower threshold.

The exemption or exclusion is below $5 million for:

5. Plan End of Year Health Expenses

Now’s a great time to plan medical expenses for the rest of the year.

If your family’s already incurred many healthcare costs this year, you may have already met your:

  • deductible or

  • out of pocket maximum.

Your costs for additional tests and procedures may be limited.

Unfortunately, other people know it’s a good time for treatment.

My wife scheduled skin cancer surgeries for years. Appointments got scarce at the end of the year. In addition to the increase in demand, healthcare professionals take time off for the holidays. 🏂


Hey, thanks for reading my post on potential steps tech professionals might take in October.

Just a reminder, I share a lot of resources that can help you.

Sign up to get the white paper:
Personal Finance for Tech Professionals


Disclaimer

In addition to the usual disclaimers, neither this post nor this image includes any financial, tax, or legal advice.

Kevin Estes, CFP®, CCFC, MBA | Founder | Scaled Finance

Kevin Estes is a financial planner helping tech professionals and their families live great lives.

He worked in T-Mobile Financial Planning & Analysis for nine years and has extensive experience with tech compensation and benefits. He received a certificate in financial planning from Boston University, passed the CERTIFIED FINANCIAL PLANNER™ exam, and founded Scaled Financed in 2022.

About | LinkedIn | Contact

https://www.scaledfinance.com/
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