What Financial Steps Might Tech Professionals Take in October 2026?
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 This Month
Financial steps tech employees might take in October include:
Evaluate employer stock
Book holiday plans
Complete open enrollment
Update estate plan
Plan year-end healthcare
1. Evaluate Employer Stock
Tech employees may have just purchased company stock at a discount. It’s worth considering what to do with those shares. 🤔
How an ESPP Works
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.
ESPP Purchase Limit
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:
RSU Vest
Many employees just had some stock vest! Those shares might fund a cash reserve.
For more, check out:
2. Book Holiday Plans ❄
Now is a great time to book holiday flights and lodging before:
vacation rentals book,
flights prices rise, or
calendars fill.
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 nearly here!
Now’s a good time to plan for 2027:
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:
4. Update Estate Plan
Halloween is a great time to update beneficiaries! 🎃
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 $15 million.
However, some states have a much lower threshold.
The exemption or exclusion is below $5 million for:
5. Plan Year-End Healthcare
Now’s a great time to plan medical expenses for the rest of the year.
If your family’s had heavy costs this year, you may have already met your:
deductible or
out of pocket maximum.
Your cost 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 year-end. 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.
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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.
