Millennial Money Expert: Stefanie O'Connell

1. What is the biggest mistake you see millennials making with their money?


Procrastination. Whether it’s procrastinating debt pay off, savings, investing or all of the aforementioned, the “I’ll get to it when” mentality among millennials is hugely problematic.

I can’t put it all on millennials though because media and culture perpetuate this image of the millennial as an 18-22 year old with nothing but time ahead of them. Even as a 30-something millennial you can find yourself buying into that notion of eternal youth, gaining a false sense of “time security” that enables procrastination of critical long-term planning.

In other words, the narrative of the millennial experience has been so shaped by the picture of youth, that millennials, regardless of age, may feel they have more than enough time to take action on long-term plans, even when they don’t.



2. What was the best lesson you had to learn the hard way?


Be aggressive with your earnings prospects. You can only cut back and save so much, but your potential for earning more is unlimited. The younger you are, the fewer commitments you have, the more risks you can take and time you can devote to fostering new income streams.



3. What drives you to help millennials with their finances?


As millennials, we grew up hearing a lot about ‘doing what you love’, but nobody talked much about the how. The value and importance of money – particularly within inspirational settings like graduation speeches and TED talks – was always overlooked

The result is a romantic notion of these concepts, which often prove impractical and difficult to sustain in the context of the real world.

When you inspire people to engage with their finances, you enable them to build a foundation that allows them to afford exploration, fulfillment, and self-actualization. We can’t just talk about the top of the hierarchy of needs, we need to engage in a discussion around the foundation upon which it is built.



4. What would you say about retirement and its preparation for millennials?


I get that when you’re making $40,000 a year in a high cost of living city, staring down a $30,000 student loan bill, the thought of setting money aside for some day after age 59.5 seems kind of crazy.

That is until you consider the cost of NOT investing.

The younger you start investing, the more you can reap the benefits of compounding and long-term market gains. Conversely, the longer you say “not yet” and wait for “someday”, the more you have to contribute later on just to catch up.


Now I know that thinking about dollars supporting some distant retirement future can seem pretty intangible when you’re a 20 something practically living paycheck to paycheck – so try thinking about it this way… Every dollar you earn through your investments is a dollar you don’t have to earn at your job. The opportunity cost of not investing now is significant and very real.




5. If a millennial is trying to take a vacation on a budget, what would you suggest?


You should never go into debt to travel and you don’t have to. Plan vacations around friends and family, try couchsurfing, rent out your room while you’re out of town to cover your costs, use airline miles to book your flights, travel in the off-season, coordinate a home swap, visit attractions during free days and hours, plan getaways around business trips, etc. There are endless ways to hack your travel costs. Just because you can’t afford the first trip estimate you come up with, doesn’t mean you can’t afford the trip. It means it’s time to get creative about your costs (and that’s true for EVERYTHING).


6. What would you say about making a budget?


Rather than driving yourself crazy calculating what you have left over to spend in each expense category throughout the month, keep things simple by defining a few key numbers for yourself.

I use a number I call the “make or break” number. Essentially, it’s the monthly minimum, no frills cost of running your life.

Here’s how to calculate it:

  • Calculate your bare bones total – the monthly cost of your necessities. That is anything you need to live and work normally.
    • Yes – food, housing, insurance, etc.
    • No – entertainment, beauty treatments, social gatherings, etc.
    • Remember to include quarterly and other irregular, essential expenses by dividing the total annual cost of those necessities by 12
  • Add a buffer. Life has a tendency to be more expensive than we anticipate. Add a buffer of at least ten percent to your monthly bare bones total.
  • Add monthly financial goal targets. How much do you want to save, invest and/or use to pay down debt each month? Include these financial targets in your make or break number so that they become as non-negotiable as your other essential expenses.

Bare Bones + Buffer + Monthly $ Goal Targets = Make or Break Number


The make or break number isn’t a budget, it’s a benchmark for the financial viability of your life. It takes into account the cost of your essential needs while keeping you committed to your long-term financial goals.


You don’t need to plot out exactly what and where you’re spending each month, but you do need to commit to earning at least as much as your make or break amount.

If your income falls short of this benchmark, you’re living beyond your means and have two choices – reduce your bare bones expenses and/or increase your earnings. 

If you surpass your make or break number, simply subtract it from your earnings to calculate how much you have to spend on discretionary expenses, i.e. wants – a new pair of sunglasses or boozy Sunday brunch for example.



7. Do you have any specific advice you enjoy giving millennials?


The only difference between knowing something and not knowing it, is taking the time to learn it. You are not stupid or bad at money, you just need to set aside the time to learn more about it. It’s not your fault that no one taught you, but it is your fault if you continue to stay ignorant about your finances.