A New Job To-Do List

With the school year approaching, I wanted to make a post for folks who might be starting a new teaching job and feeling overwhelmed with everything. First, congratulations! You’ve joined a wonderful profession! Thank you for the time, dedication, and heart that you've already committed.

When it comes to personal finance, my experience has been that new teachers often get minimal guidance related to benefits. Unless you are someone who enjoys digging through pdfs, reading spreadsheets, and examining fine print*, you likely won't have much engagement with specifics apart from surface-level comments at an orientation meeting. This is problematic because the benefit decisions you make now can have significant short-term and long-term financial consequence. Moreover, as I mentioned in Focus Less on Numbers, the first few years in the teaching profession can be overwhelming as you learn the trade (e.g., lesson planning, assessment, classroom management) and navigate big life changes that might be happening. If you are feeling this way, please give yourself grace and kindness. 

Three steps to focus on with a new job.

This post is intended to be a to-do list of important items for folks starting a new job. My comments are aimed at Wisconsin educators, but should be generally applicable. Like everything personal finance, your context will make certain things more or less relevant. I've organized the discussion into three steps: Find Key Documents, Decide on Medical Coverage, and Review Retirement and Life Insurance Options.

Step 1: Find Key Documents

1. The Employee Handbook

Your district should have some kind of handbook. It may be publicly available or internal. This is your go-to resource for policies, benefits, and procedures. Focus on sections about leave, pay schedules, and benefits. The handbook might also list district-specific perks, like health clinics or service-based retirement contributions.

2. Pay Schedule

Knowing how and when you are paid is essential in making decisions. Is your salary spread over 12 months or paid during the school year only? If you're on a 12-month schedule, your monthly income is lower but more consistent. If you are on a 10-month schedule, you'll have a few months without pay. How will you handle this? Two approaches are to save up several months of living expenses or set up an automatic transfer to your own summer savings fund. This one decision can affect your budgeting, saving, and peace of mind over the entire year.

3. Salary Schedule

Every district should have some kind of salary schedule that outlines how your pay increases with years of experience and education level. It’s important to find and review this document early on because it can help you plan your career growth and understand how raises and steps work. Knowing your salary schedule can also guide decisions about pursuing additional certifications or advanced degrees.

Step 2: Decide on Medical Coverage

1. Health, Vision, and Dental Plans

During onboarding, you’ll be asked to select your insurance options. The options you select affect your take-home pay and access to care all year long. If you’re enrolling in coverage, compare premiums, deductibles, and coverage between plans. Choose what fits your actual health needs, not just what others around you pick. If you’re declining coverage, check if your district offers an opt-out payment. For those under 26 who can still be covered by a parent, this might provide some extra income for a few years.

2. Flexible Spending Accounts (FSA)

If your district offers a health care or dependent care FSA, you can set aside pre-tax dollars for eligible expenses. Common eligible expenses include: doctor co-pays, prescriptions, dental work, vision care, and childcare. This lowers your taxable income and helps those pretax dollars go farther. However, you  should have some clear expenses in mind when choosing to enroll because unused funds may be forfeited at the end of the plan year.

3. Health Savings Account (HSA)

If you choose a high-deductible health plan, you may qualify for an HSA. Like an FSA, contributions are pre-tax (or tax-deductible), but funds roll over year to year and can be invested for future health expenses. HSAs can be a powerful long-term savings tool often described as triple-tax advantaged. That said, your context should guide you on whether an HSA is a good choice.

Step 3: Review Retirement and Life Insurance

1. Wisconsin Retirement System Variable Option

When you start with the Wisconsin Retirement System (WRS), you’ll be automatically enrolled in the Core Fund unless you opt to put a portion of your contributions into the Variable Fund. The Variable Fund includes more exposure to equities (stocks), which historically have higher long-term returns. Choosing the Variable option early in your career gives your retirement contributions more ability to grow especially if you're 2+ decades away from retirement. You can always opt out if your risk tolerance changes. Read my post on The Pension Path for a general idea about how WRS works.

2. Life Insurance Options

If you do not have children, a mortgage, or folks who are dependent on your income, you probably don’t need much life insurance right now. As a member of the Wisconsin Retirement System, you will have a death benefit. For active employees, this benefit is the total account value. For inactive employees, it is a partial account value. The first few years, this benefit won't be much, but afterwards it should provide a modest amount of coverage. More information on the WRS Death Benefit here. 

If you have children, a mortgage, dependents, etc., some additional life insurance might be warranted. Check if your employer offers the The Wisconsin Public Employers Group Life Insurance, it’s affordable, and for most young educators it’s likely enough. If you start looking at private insurance, term life insurance is usually the most cost-effective option.

3. Supplemental Retirement Options

Your district likely offers access to a 403(b) plan and might offer access to a 457(b) retirement plan (also called the Wisconsin Deferred Compensation Program). These options are typically self-funded although I know of one district that provides yearly contributions as an incentive to retain teachers. Unless your district matches or contributes to these accounts, you may want to hold off and focus your savings elsewhere. One reason being that you might have limited options in terms of the investments available within the account. Additionally, the management fees for some plans can be high. If you do decide to save using one of these plans, the 457 has one key advantage: You can withdraw funds from a 457 without penalty if you separate from your employer, even if you're under 59½. That flexibility can be a big deal if you switch careers, take a break, or retire early.

4. Roth IRA

This likely isn't a benefit you will see discussed in employment materials but if you are able to make additional savings for retirement, a Roth IRA is probably the best place to start. In a future post, I plan to talk about how a Roth IRA works well with a typical teacher's financial context. For now, here are a few reasons I think it is worth pursuing:

  • You control it. Unlike a district-sponsored plan, you choose the provider, investment options, and fees. You can pick a low-cost brokerage (e.g., Schwab, Vanguard, Fidelity) and use low-costs index funds.
  • It’s flexible. You can withdraw your contributions (not earnings) at any time without penalty. It can serve as a funding source early retirement or a last-resort backup emergency fund.
  • Spousal contributions are allowed. If you're married and your partner has little or no income, you can contribute to a Roth IRA for them too. If you take a few years off, they can make the contributions for you.
  • It’s tax-advantaged. Contributions are after-tax, but qualified withdrawals in retirement are tax-free.
If you're new to investing and wondering where to start, I highly recommend reading A Simple Path to Wealth by JL Collins. It’s a helpful guide that aligns well with the realities of a teaching salary.

In Summary

As an educator, you likely have access to some valuable benefits. However, you might feel overwhelmed by the options available and pressure to make quick choices so you can focus on other things. I hope you can use this post as a starting point to help guide decisions the first year. Remember to return to these steps with each new contract and as your context evolves. To recap:

  1. First: Find Key Documents
    1. Employee Handbook
    2. Pay Schedule
    3. Salary Schedule
  2. Second: Decide on Medical Coverage
    1. Health, Vision, and Dental Plans
    2. Flexible Spending Accounts (FSA)
    3. Health Savings Account (HSA)
  3. Third: Review Retirement and Life Insurance Options
    1. Wisconsin Retirement System Variable Option
    2. Life Insurance Options
    3. Supplemental Retirement Options
    4. Roth IRA

Wishing you a great school year! 

First posted August 10, 2025

*When I got my first job, I remember looking through all the benefits documents with a sense of excitement. Your mileage may vary :D 

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