In 1997, Tina Fey left her home in Chicago for a job interview.

Looking back, she says, “A couple of times I’ve been called on to do things — jobs or whatever — where I’ve felt, maybe I’m not quite ready. Maybe it’s a little early for this to happen to me.”

Fey arrived at the job interview in “the only decent clothes” she owned at the time. She slowly walked up to the security guard at the elevator. And then, in total disbelief, heard herself say aloud:

“I’m here to see Lorne Michaels.”

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Tina Fey’s career began at an improvisational acting school.

And beginners’ improv revolves around four informal rules. The rules teach aspiring comedians how to create something together on stage. Out of loosely-defined ideas, interests, and individual perspectives, something very real (and funny) can emerge.

But as Fey notes in her book, Bossypants, she valued the rules of improv for more than just crafting jokes. The rules also appealed to her as a worldview. The things she learned in that improv school, she says, “became part of the way I live my life.”

Improv can help us create something with our money, too. Out of loosely-defined ideas, interests, and individual perspectives, something very memorable (and satisfying) can emerge.

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The First Rule of Improv: Always Agree

Improv thrives on creating opportunities from whatever circumstances and resources exist. Fey explains:

“When you’re improvising, this means you are required to agree with whatever your partner has created. So if we’re improvising and I say, ‘Freeze, I have a gun,’ and you say, ‘That’s not a gun. It’s your finger. You’re pointing your finger at me,’ our improvised scene has ground to a halt. But if I say, ‘Freeze, I have a gun!’ and you say, ‘The gun I gave you for Christmas! You bastard!,’ then we have started a scene because we have agreed that my finger is in fact a Christmas gun.” 

Think about times when you’ve checked your savings account balance. Have you ever felt a tiny rush of dopamine over the amount sitting there?

Saving money is, of course, a valuable habit. But so, too, is using your savings when you can create the life you desire. Yet, many diligent savers stress out about withdrawing these funds. If a partner suggests a work sabbatical or an extended trip abroad, these savers are more likely to respond, “That’s just your finger. You’re pointing your finger at me.”

But at various times in life, you need to start that improv scene. You should give your partner’s ideas a chance. As Fey says, “Start with a ‘yes’ and see where that takes you. …I always find it jarring when I meet someone in real life whose first answer is no. ‘No, we can’t do that.’ ‘No, that’s not in the budget.’ …What kind of way is that to live?”

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The Second Rule of Improv: Say “Yes, And…”

In improv, you must do more than merely agree. You must “add something of your own.” Here’s how Fey describes it:

“If I start a scene with ‘I can’t believe it’s so hot in here,’ and you just say, ‘Yeah…’ we’re kind of at a standstill. But if I say, ‘I can’t believe it’s so hot in here,’ and you say, ‘What did you expect? We’re in hell.’ Or… you say, ‘I told you we shouldn’t have crawled into this dog’s mouth,’ now we’re getting somewhere.” 

Being able to say “yes” is an essential aspect of using your money to live your ideal life. But on its own, it’s too passive. Especially if you’re making decisions with a partner, kids, parents, or friends.

You’ll likely hit a standstill in your financial planning if you never voice your values. “Yes, and…” creates the freedom to explore your interests. And you should empower your loved ones to do the same. These open conversations certainly may feel contentious at times. But they’re the only way to start making progress toward what each of you want out of life.

In fact, Fey argues, “it’s your responsibility to contribute.”

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The Third Rule of Improv: Make Statements

Yet, becoming more open to potential opportunities is not the same as making them happen. Fey writes: 

“If we’re in a scene and I say, ‘Who are you? Where are we? What are we doing here? What’s in that box?’ I’m putting pressure on you to come up with all the answers. In other words: whatever the problem, be part of the solution. Don’t just sit around raising questions and pointing out obstacles. …Instead of saying ‘Where are we?’ make a statement like ‘Here we are in Spain, Dracula.’”

Our finances demand that we constantly ask good questions:

• “What do these terms mean?”
• “Is this account or that account better for me?”
• “What are the risks I should know?”

But questions become secondary when we’re envisioning and talking through our ideal life. Too often, we allow uncertainty – those where, what, how questions – to lock us into the status quo. If your partner proposes a work sabbatical in two years, your initial, natural reaction may be to question the idea. But Fey suggests that you instead “make statements, with your actions and your voice.”

This is the bridge we must cross to become part of the “solution” in spending our money for the greatest personal impact.

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The Fourth Rule of Improv: There Are No Mistakes

Improv creates the space for “mistakes” to serve as opportunities. The outcome may look different than the comedians anticipated. But that doesn’t mean the scene won’t change in positive ways. Fey says:

“If I start a scene as what I think is very clearly a cop riding a bicycle, but you think I am a hamster in a hamster wheel, guess what? Now I’m a hamster in a hamster wheel. I’m not going to stop everything to explain that it was really supposed to be a bike. Who knows? Maybe I’ll end up being a police hamster who’s been put on ‘hamster wheel’ duty because I’m ‘too much of a loose cannon’ in the field.” 

Likewise, we also can turn into opportunities the financial decisions that we fear will become mistakes. Sure, the outcome may look different than we hoped. But that doesn’t mean our lives still won’t change in positive ways.

When you take a thoughtful approach to spending money, you likely will find yourself content with many of the decisions you’ve made. And those “regrets” that you fear in advance ultimately can play a more helpful role than you realize.

We often discover what we value and enjoy in life through the simple act of trying. A new hobby, different restaurant experience, or adventurous trip will feel like a disappointment once in a while. But that doesn’t mean you made a mistake. Who knows? Maybe those experiences will guide you toward the uses of your money that do feel especially rewarding.

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Tina Fey rode that elevator up to Lorne Michaels’ office and her job interview. And not too long after, she received a call saying, “We’re offering you a job here at Saturday Night Live — can you move here within a week?”

Fey could have held off on pursuing that interview. She could have said that moving and starting a high-profile job within one week was too much. But she responded differently due to the improv rules ingrained in her mind.

And, like she told Michaels — and as we should say more often with our money:

“Ummm, yes I can.”

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About the author: Kevin Mahoney, CFP®

Hi, I’m Kevin. I’m a financial advisor in Washington, DC. I’m also the founder of Illumint, an independent financial planning company in the District that specializes in financial planning for Millennials like you. I empower our generation with the confidence to invest an inheritance, financial gift, or extra savings. If you’re new to Financially Well, welcome – you now have access to the leading finance podcast for Millennials. I encourage you to read, watch, or listen to the ideas I’ve shared about making your money work for you. And then when you’re ready, please send me your thoughts & questions!