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The Questions I Ask Myself When Making Tough Decisions

The Questions I Ask Myself When Making Tough Decisions

I’ve had to make some tough decisions in my career. For example, should we institute a big lay-off in 2010, or double-down by hiring more trainees? (More trainees.) Should I fight my boss to return client funds, lost in poorly constructed products in the 2008 downturn? (I did, and lost my job over it.) After that, should I return to big business or start my own business? (I’ve started Ellevest, a digital investment platform targeted to women.)

I’m sometimes asked how I work through tough, high-stakes decisions. I do all of the analyses you might expect; I work though all the pluses and minuses. But here are three questions that I always ask myself, and always give me some clarity:

1) What is my stomach telling me? Over the years, I’ve found that my stomach tends to figure things out before my head does. Sometimes well before my head does.

Stomach hurting on Sunday night? You’re getting a message. Head aching in meetings about a strategic shift? Same. Once my stomach starts to hurt, I know something is off; it’s up to me then to figure out what’s wrong, and what action to take.

2) What would the person-I-want-to-be do? For you, maybe the person-you-want-to-be is your role model. A person you looked up to at school, perhaps one who acted with kindness or integrity. Maybe it’s your parent or grandparent, or a coach. Maybe it’s someone you want to make proud. Or maybe it’s the person you’re on your way to becoming, or a better version of yourself.

I always ask myself: What would he/she do?

3) What would the person-I-want-my-children-to-believe-I-am do? I’ve written before about “Why You Should Work as Though Your Kids are Watching.” If you have to explain this decision to them, what are they going to think? What is that dinner conversation going to be? If they were able to Google you – or Google this choice and its impact – what will their reaction be?

This article previously appeared on LinkedIn.


Sallie Krawcheck is the Co-Founder and CEO of Ellevest. You can sign up for early access here. She is the Chair of Ellevate Network, the global professional women’s network.

For information about Ellevest, a Securities and Exchange Commission (SEC) registered investment adviser and its financial advisory services, please visit the firm’s website ( or the SEC’s Investment Adviser Public Disclosure website (

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