Webinar | Confused by retirement planning? You’re not alone. Aug 10, 2026
Jul 10
6 min read
Updated: Aug 17
From 401(k)s and Roth options to planning for freelancers, entrepreneurs and those without employer-sponsored plans, today’s retirement landscape can feel overwhelming.
WISE brought together retirement experts from State Street Investment Management and WISE for a practical conversation designed to help women better understand their options, avoid common mistakes and make more informed decisions about their financial future.
Why watch the replay?
You’ll walk away with practical insights on:
Making the most of 401(k)s, Roth options and employer-sponsored plans
Retirement planning strategies for freelancers and entrepreneurs
Common mistakes and misconceptions that can impact long-term savings
Ways to build greater retirement security at every stage of life and career
Actionable ideas to help you take greater control of your financial future
This was one of those conversations everyone wishes they had earlier. Watch the replay and get WISE about retirement.
Webinar Recap: Demystifying Retirement Plan Options
WISE hosted this webinar as part of its “Retirement Reimagined” series, in partnership with State Street Investment Management. The discussion featured Elise Thaman, Vice President at State Street Investment Management, and Tina Shackman, Senior Retirement Plan Consultant at Benefits Financial Services Group and WISE board member.
The central message was simple: retirement planning can feel complicated, but a few good decisions made consistently—especially starting early, saving regularly, diversifying, and understanding taxes—can have an enormous impact.
Why retirement planning is especially important for women
The webinar opened with an interesting contradiction. Women tend to participate in 401(k) plans at higher rates than men, save at slightly higher rates, trade less frequently, and—according to a Fidelity study cited in the presentation—have historically outperformed men by about 0.4% per year.
Yet women still tend to retire with less money.
The presenters cited average retirement balances of approximately $195,000 for men versus $146,000 for women, along with about $4,800 less per year in Social Security benefits for women.
At the same time, women live roughly five years longer on average.
The presenters attributed much of this gap to differences in lifetime earnings and time outside the workforce for caregiving. Leaving the workforce doesn't just mean losing wages—it can also mean losing employer retirement contributions, investment growth, and Social Security earnings credits.
Traditional vs. Roth retirement savings
One of the most useful portions of the webinar was the explanation of the two basic tax strategies.
With traditional/pre-tax contributions, money goes into a workplace retirement account before income taxes are paid. It grows tax-deferred, and withdrawals during retirement are generally taxed as ordinary income.
With Roth contributions, taxes are paid today. The money then grows in the Roth account, with qualified withdrawals potentially coming out federal-income-tax-free later.
The presenters emphasized that this doesn't necessarily have to be an either/or decision. Having both pre-tax and Roth retirement money can provide greater flexibility in retirement.
They also discussed IRAs as another way to save outside an employer-sponsored plan.
Take full advantage of your employer plan
A recurring message was: if your employer offers a match, try to contribute enough to receive the entire match.
In the webinar poll, 63% of respondents said they were contributing enough to receive their full employer match, while 7% were not. About 30% said their employer didn't offer a matching contribution.
The presenters also recommended gradually increasing contributions rather than waiting until you feel you can suddenly afford to save significantly more.
One strategy is to increase your contribution by 1% whenever you receive a raise. Some retirement plans can even automate these annual increases.
They also highlighted catch-up contributions for older workers as an important opportunity to accelerate retirement savings.
Understanding your investment choices
The webinar broke retirement investments into three basic asset classes:
Cash → lowest volatility, but generally the lowest long-term growth potential.
Bonds → essentially loans to companies or governments. They typically fluctuate less than stocks but generally offer greater growth potential than cash.
Stocks → ownership in companies. They have historically offered greater long-term growth potential but can fluctuate considerably.
Most retirement-plan participants aren't buying individual stocks and bonds. Instead, they invest through funds containing many different investments.
The presenters discussed four common fund types: capital-preservation funds, actively managed funds, index funds, and target-date funds.
Target-date funds received particular attention because they're designed as a relatively hands-off retirement solution. Investors choose a fund associated with approximately when they expect to retire, and the fund gradually changes its allocation as retirement approaches—generally moving from more growth-oriented investments toward more conservative ones.
Don't try to time the market
This was another major theme.
Selling when markets fall and trying to buy back at the right moment can seriously hurt long-term returns because some of the market's strongest days occur near its worst days.
The presenters showed an example comparing someone who remained invested for 20 years with someone who missed only the 10 best market days. Missing those few days resulted in dramatically less wealth.
Their message was essentially: time in the market matters more than trying to perfectly time the market.
This becomes particularly important during frightening market declines.
What happens to your 401(k) when you leave a job?
Leaving an employer doesn't necessarily mean you have to immediately move your retirement account.
Depending on the plan, options can include leaving the money where it is, rolling it into another retirement plan or IRA, taking partial withdrawals, establishing installment/systematic withdrawals, or taking a lump sum.
The presenters also discussed Roth conversions.
Converting pre-tax retirement money into Roth money can create a significant taxable event. Because of that, a lower-income year may sometimes present an opportunity to consider a partial Roth conversion. They emphasized that this is something to evaluate carefully rather than automatically converting an entire account.
The five retirement mistakes to avoid
The webinar boiled much of its advice down to five major mistakes:
Starting too late. Compounding becomes extraordinarily powerful when given decades to work. Their example compared someone beginning at 24 with someone beginning at 35 while contributing the same $100 per month. The earlier saver ended up with more than $200,000 additional savings in the example.
Not saving enough. Small increases matter. Increasing retirement contributions by even 1% at a time can accumulate into substantial differences over a career.
Failing to diversify. No single asset class consistently wins every year. Diversification spreads risk, while periodic rebalancing prevents a portfolio from accidentally becoming much riskier than intended.
Underestimating retirement expenses—especially healthcare. The presenters cited an estimated roughly $330,000 in out-of-pocket healthcare expenses for a married couple during retirement, emphasizing the need to account for healthcare when determining how much retirement will actually cost.
Ignoring taxes. Retirement isn't simply about accumulating the largest possible account. Where the money is held—and how withdrawals will eventually be taxed—also matters. Having taxable, tax-deferred, and Roth assets can create more flexibility.
Highlights from the Q&A
The audience asked several particularly practical questions.
For self-employed people, the presenters discussed Solo 401(k)s, state-sponsored auto-IRA programs, and Pooled Employer Plans (PEPs). PEPs may allow smaller employers to participate in an existing plan structure rather than handling all of the administration themselves.
They also clarified that IRA contributions generally require earned income.
For people who started saving later in life, their advice was not to panic or compensate by taking excessive investment risk. Instead, look at catch-up contributions, increasing savings, reducing spending, potentially adjusting retirement expectations, and getting professional planning help.
They also mentioned deferred annuities as one potential tool for generating income later in retirement, while specifically noting that they weren't recommending a particular product.
Social Security shouldn't be forgotten either. Delaying Social Security can increase eventual monthly benefits and should be considered as part of the overall retirement-income picture.
Finally, they addressed one of the biggest fears for people approaching retirement: What happens if the market crashes right before I retire?
Their advice was generally not to panic and abandon the investment strategy. Retirement doesn't mean withdrawing an entire portfolio on day one. Even at retirement, much of the portfolio may remain invested for years or decades.
For someone already taking withdrawals, they suggested that—when financially possible—reducing withdrawals during a major market decline may help avoid selling investments after losses and give the remaining portfolio time to recover.
Biggest takeaway
The webinar wasn't really about finding the "perfect" retirement investment.
It was about building good retirement habits:
Start early. Save consistently. Capture the employer match. Increase contributions as income rises. Diversify. Don't panic during market declines. Understand the tax consequences of traditional vs. Roth savings. Plan for healthcare. And know the actual rules and features of your retirement plan.
One particularly useful suggestion at the end was that you don't necessarily need an ongoing financial-advisor relationship. Someone approaching retirement could consider paying for a one-time professional review of their retirement strategy to identify problems or opportunities before making major decisions.
The webinar's overall message could probably be summed up as: you don't need to become an investment expert to improve your retirement outcome—but you do need to start, understand your options, and remain consistent.
