The Upside

Investing in Yourself: Overcoming Guilt and Achieving Growth

Last week I had lunch with a colleague who sparked a conversation that made me think of you and many Upside community members as well.

She was talking to me about how she doesn’t like to spend money on herself or her business because she feels like she’s taking away from something else…

…and that she doesn’t really deserve or need these things.

I think a lot of us have these thoughts – heck, I definitely do.

We think that by investing in ourselves, our well-being, our business, or even on a splurge item, we’re taking away from our other responsibilities.

However, ask any CEO of a successful business how he or she got to the top and I guarantee you that one or more of their answers points to spending on themselves, like:

  • An Ivy League MBA program that expanded their network with the right people
  • A 5-figure/year business cohort that kept them focused on making smart decisions
  • A 1:1 coach that taught them how to lead with confidence and empathy
  • A new VA who was a big investment, but gave them back priceless hours of time
  • A new work outfit that was a splurge, yes,  but gave them confidence on a big stage

If you’ve been putting off an investment in yourself or your business because you feel guilty spending the money, then know you are not alone.

But when you’re feeling this guilt, try using the exercise below to unpack those feelings and get clarity on whether or not you should go for it:

I hope you’ll print this out and pin it to your bulletin board…

…because as the saying goes: sometimes you have to spend money to make money.

Erin Halper

About the Author

Erin Halper is the founder and CEO of The Upside and the leading authority on independent consulting. Since launching The Upside in 2017, Erin has helped thousands of professionals transition from corporate life into consulting to achieve flexibility, autonomy, and a renewed sense of purpose in their careers.

Erin has been a frequent speaker at Columbia, NYU, Harvard, and Brown and has been featured as a leading future of work expert on dozens of podcasts as well as in Forbes, Business Insider, Nasdaq, Crunchbase and many more.

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