Investing and Retirement Planning Workshop Syllabus (Winter 2026)

This is a rough approximation of what we’ll cover each day, but topics may move around depending on how far we get each day.

Day 1

The problem

  • Why retirement planning is such a mess

  • Challenges for creative types and freelancers

  • Challenges for women (so many…)

  • Challenges for people from marginalized groups

Investing 101

  • “Safe” assets: High-yield savings accounts, CDs, money market funds

  • The giant, slobbering maw of inflation

  • Stocks: Dividends and capital gains

  • Bonds, bonds, bonds: Federal, municipal, corporate! Short, intermediate, long-term!

  • The risk/reward trade-off

  • Actively managed funds: The pros know what they’re doing, right?

  • The “small” fees that can cost you hundreds of thousands of dollars

  • Thank god for index funds

  • A simple 3-fund portfolio

Your biggest decision

  • Choosing an asset allocation (aka, how much are you going to freak out when the stock market crashes?)

  • Old and new rules of thumb

  • Willingness, ability, and need to take risk

  • Let’s take a quiz!

  • A quick look at international stocks

  • Roberta’s decision: How I chose my asset allocation

Day 2

Target date funds

  • What’s under the hood?

  • Choosing the fund that’s right for you (not just the default)

  • Should I stick with target date funds? Pros, cons, and personal preferences

Allll the accounts

  • It’s all about the tax breaks

  • For freelancers: SEP IRA vs solo 401(k), and how to not screw up your employer contribution

  • For employees of organizations: The airplane meals of retirement accounts

  • All things Roth: Backdoor Roth, Roth conversions, and new Roth contribution options

  • IRAs and the secret spousal contribution

  • What to do with zombie 401(k) accounts

  • HSA! HSA!

Nuts and bolts

  • But how do I actually do this?

  • Brokerage firms (the supermarkets) and fund providers (the brands)

  • Buying funds (it’s like any other online shopping… but with one extra step)

  • Mutual funds vs exchange-traded funds (ETFs)

  • Avoiding nasty tax surprises

Your nest egg target

  • The two most important numbers

  • Sequence of returns risk: Let’s try not to die broke

Day 3

Your nest egg target

  • The 4% rule, or what retirement planning experts like to argue about at cocktail parties

  • Your vision for retirement: Bingo nights or grand world tour?

Social Security

  • Getting an estimate of your benefits

  • Social Security’s most amazing feature: The cost-of-living adjustment

  • But isn’t it all going away?

  • Roberta’s decision: My somewhat but not extremely conservative plan for Social Security

Am I on track?

  • Estimating investment returns: Historical data vs the cloudy crystal ball

  • There’s absolutely no way I can save that much, now what?

  • How not to run an online retirement calculator: Parameters and pitfalls

  • 5 retirement calculators that I don’t hate

Stress-testing your plan

  • How expenses actually work in real life

  • Saving for your dreams

  • Planning for income dips/plateaus: Parental leave, caregiving for parents, long-term passion projects, creative sabbaticals, extended time off, aging, ageism

  • Things we’d rather not think about that might happen when we get old

Looking ahead

  • Boring/confusing things we might need one day: Annuities and reverse mortgages

  • How to find a trustworthy financial advisor

Image credit: ArisSu