What Financial Steps Might Tech Professionals Take in September?

Fall foliage background with a partially transparent white box. Title: "September" on top. It's a checklist with Select ESPP contribution %, Book Thanksgiving plans, Start benefits review, Replenish cash reserve, and Schedule remaining PTO.

How is it September already?

Fortunately, we still have a third of the year left!

September Financial Steps

Potential steps tech employees might take in September include:

  1. Select ESPP contribution %

  2. Book Thanksgiving plans

  3. Start benefits review

  4. Replenish cash reserve

  5. Schedule remaining PTO

1. Select ESPP Contribution %

Participating in an Employee Stock Purchase Plan (ESPP) isn’t right for everyone. Nonetheless, it’s worth considering.

The primary benefit may be a 15% discount off the lower of the price at the beginning and end of six months.

Let’s say a stock’s price is $200.

  • If the stock stays the same over six months, it would be purchased at $170 and have a built-in $30 gain.

  • If the stock price rises to $220, it would be still purchased at $170 and have a larger built-in $50 gain.

  • If the stock price falls to $180, it would be purchased at $153 and have a smaller built-in $27 gain.

Disadvantages

Some disadvantages of participating in an Employee Stock Purchase Plan include that it:

  • reduces cash flow,

  • locks up money (usually until purchase), and

  • increases taxes - especially if shares are sold right away.

What If I’m Laid Off?

Unfortunately, layoffs are a constant threat at tech companies. There’s both bad and good news.

  • Bad news: a participant no longer employed on the purchase date misses the opportunity to buy at a discount.

  • Good news: the participant will instead get the cash back. It’s almost like a small - yet growing! - emergency fund.

For more, check out:

How Does an ESPP Work?

Are ESPPs Underrated?

Own Stock or Contribute to ESPP?

2. Book Thanksgiving Plans

It’s important to plan ahead for Thanksgiving travel:

  • Hotels and short-term rentals fill up, especially at popular locations.

  • Last-minute flights are normally more expensive.

  • People get busy.

Avoid the drama. 🎭 Book now.

3. Start Benefits Review

Open enrollment starts soon! Now’s a good time to check your benefits.

Are you expecting any major expenses?

  • This year: If you’ve already met your health insurance deductible, it may make sense to pull forward healthcare expenses into 2026.

  • Next year: You may need to increase your coverage to pay for higher upcoming expenses.

Do you have “use it or lose it” funds?

  • FSA = Flexible Spending Account. Funds need to be used in 2026. (There’s a possible $680 carryover)

  • HRA = Healthcare Reimbursement Arrangement. Funds may also need to be used in 2026, though it depends on the plan.

  • HSA = Health Savings Account. Funds are NOT “use it or lose it” and don’t to be spent this year.

If you currently have a large FSA or HRA balance, would it make sense to reduce your contribution with open enrollment?

For more, check out

Pros and Cons of a Health Savings Account

How Disability Insurance Works!

4. Replenish Cash Reserve

Huzzah for all you did this summer!

Those activities may have shrunk your cash reserve. Now could be a good time to top it off before the holidays.

Restricted Stock Units

RSUs may vest more than once a year, which is good news. 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?

Social Security Maximum

Reaching the Social Security income maximum of $184,500 for 2026 might also help! About 6% of covered workers earn more than the Social Security taxable income each year.

5. Schedule Remaining PTO

“Use it or lose it” doesn’t just apply to spending and reimbursement accounts.

Paid Time Off (PTO) is there for a reason. Use it!

Employees might roll over up to two weeks (80 hours). However, that limit can fluctuate. At T-Mobile, it was:

  • as low as 40 hours and

  • as high as 120 hours (COVID-19, merger).

Play it safe and plan to carry over no more than 40-80 hours.

Scheduling PTO early also helps avoid scheduling conflicts with teammates. Call dibs!

Hey, thanks for reading my post on potential financial steps for tech professionals in September.

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

Join the newsletter and get the white paper:
Personal Finance for Tech Professionals


Disclaimer

In addition to the usual disclaimers, neither this post nor these images include any financial, tax, or legal advice.

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

Kevin Estes is a financial planner in near Seattle who helps tech professionals and their families live great lives.

He has first-hand experience with tech compensation and benefits from his past roles at T-Mobile and Amazon. Kevin holds a B.A. in Economics and Political Science from UCLA, an MBA from the University of Notre Dame, and a certificate in financial planning from Boston University. He founded Scaled Finance, LLC in 2022.

About | LinkedIn | Contact

https://www.scaledfinance.com/
Next
Next

What Financial Steps Might Tech Professionals Take in August 2026?