Invest in Your Career: How to Maximize Your Benefits
COUCHSIDE CONVERSATIONS

Invest in Your Career: How to Maximize Your Benefits

Invest in Your Career: How to Maximize Your Benefits

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COUCHSIDE CONVERSATIONS

Featuring

Beau Wirick, Wealth Advisor at Morton Wealth

Mike Rudow, Wealth Advisor at Morton Wealth

Your salary is only one part of your compensation. As your career progresses, benefits like a 401(k), company stock, an HSA, and employer-provided insurance can become meaningful parts of your financial picture, but understanding how to use them isn't always straightforward.

In this episode of Couchside Conversations, Modearn™ Advisors Mike Rudow and Beau Wirick break down several common employee benefits and the financial planning decisions that come with them. They compare traditional and Roth 401(k)s, explain employer matching and equity compensation, explore the tax advantages and tradeoffs of HSAs, and discuss what to consider when evaluating life and disability insurance. The conversation provides a practical framework for understanding what your employer offers and how those benefits may fit into your broader financial plan.

Key Takeaways

  • Choosing between a traditional and Roth 401(k) often comes down to taxes now versus later. A traditional 401(k) provides a current tax deduction, while Roth contributions are made after tax but can provide tax-free qualified withdrawals in retirement.
  • Your employer match can be an important part of your retirement savings strategy. Mike explains how different matching structures work and why building both traditional and Roth retirement assets can provide more flexibility when managing taxable income in retirement.
  • Equity compensation can create opportunity and concentration risk. With RSUs, Beau suggests asking whether you would buy your company's stock if you had received the same amount in cash, particularly when company stock already represents a significant portion of your investable net worth.
  • Stock options require careful attention to timing and taxes. Non-qualified stock options can create ordinary income when exercised, and decisions about when to exercise or sell may depend on the stock price, your income, tax bracket, and broader financial situation.
  • HSAs offer unique tax advantages, but the health plan still needs to make sense for you. Contributions can be deductible, investments can grow tax-free, and qualified medical withdrawals can be tax-free, but eligibility requires a qualifying high-deductible health plan that may not fit everyone's healthcare needs.
  • Employer-provided insurance should be evaluated alongside your family's actual needs. Life and disability coverage can have different tax consequences depending on who pays the premiums, and some group policies may not follow you if you leave your employer.

Watch the Full Conversation

Watch previous episodes here:

Buying a Home vs. Investing in Property

Managing the Cost of Having Children

Key Moments from this Episode

02:03 – Traditional vs. Roth 401(k): Understanding the Tax Tradeoff
Mike explains how traditional and Roth 401(k)s are taxed differently and why your current versus expected future tax bracket can help inform which approach makes sense.

06:16 – Making the Most of Your Employer 401(k) Match
Employer matching can add meaningful value to your retirement savings. Mike and Beau also discuss how building both traditional and Roth assets can create greater tax flexibility later.

08:53 – RSUs and the Risk of Too Much Company Stock
Beau breaks down how RSUs work and why holding significant company stock can create concentration risk when both your income and investments depend on the same company.

13:17 – How Non-Qualified Stock Options Work
Mike and Beau walk through vesting, grant prices, exercising options, and the tax considerations that can influence when you choose to exercise or sell.

17:23 – The Triple Tax Benefit of an HSA
HSAs can offer tax-deductible contributions, tax-free growth, and tax-free qualified medical withdrawals, but Beau explains why a high-deductible health plan still needs to fit your healthcare needs.

20:13 – Evaluating Life and Disability Insurance Through Work
Employer coverage isn't automatically enough. Mike discusses taxes, portability, dependents, income replacement, and other factors to consider when determining how much protection your family may need.

Questions this Episode Answers

  • Should I keep my RSUs or sell them when they vest?
    • Beau suggests asking yourself: if you received the same amount in cash, would you use it to buy your company's stock? Your existing exposure to the company and the concentration risk within your overall investments should also factor into the decision.
  • Why would I want both traditional and Roth retirement savings?
    • Having both can provide more flexibility in retirement by giving you different sources to draw from depending on your tax situation. Mike notes that this can help with managing taxable income as you begin spending your retirement assets.
  • How can I tell if I have too much of my net worth invested in my employer's stock?
    • Beau suggests looking at company stock as a percentage of your investable assets and notes that a position above 10% deserves careful consideration. The risk is amplified because your salary and a significant portion of your investments may depend on the same company.
  • Do I have to exercise my stock options as soon as they vest?
    • Not necessarily. Mike explains that vested options may provide a longer window to exercise, allowing you to consider the stock price, grant price, income, and potential tax impact before deciding when to act.
  • Can I use an HSA as part of my long-term savings strategy?
    • Potentially. Beyond paying current medical expenses, HSA funds can be invested and grow tax-free, and Beau discusses how the account can become another long-term savings bucket for those already maximizing other tax-advantaged opportunities.

Why This Matters for Investors

As your career grows, your compensation can become much more complicated than the number on your paycheck. A 401(k) match, RSUs, stock options, an HSA, and insurance benefits can all create opportunities, but each comes with decisions that can affect your taxes, investments, and family's financial security.

This episode helps turn those benefits into decisions you can more confidently evaluate. Mike and Beau explain what to look for, where potential tradeoffs and risks can arise, and why the best choice may depend on your career stage, tax situation, healthcare needs, and family. For Millennials and Gen X building wealth, understanding the benefits you've already earned can be an important part of making your career work harder for your broader financial plan.

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DISCLOSURES

Information presented herein is for discussion and illustrative purposes only and is not intended to constitute financial advice. The views and opinions expressed by the speakers are as of the date of the recording and are subject to change. These views are not intended as a recommendation to buy or sell any securities, and should not be relied on as financial, tax, or legal advice. You should consult with your finance professional, accountant, or tax professional before implementing any transactions or strategies concerning your finances.