CategorySuccess Guilt

My business just sold to a $100 million private equity fund and I still found myself feeling like a fake

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The webinar business I co-founded over 14 years ago just completed due diligence and closed its sale to a $100 million private equity fund that specializes in SaaS (Software as a Service), and now that particular part of my life is done. Even though I exited an active role with the company several years ago, I still retained 50% ownership and monthly dividends from that. It feels good to have...

Attach *RED ALERTS* to these specific words

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There are 2 words/phrases that almost always show up when I’m feeling bad about myself: Should and Supposed to “I should be working harder on my book” Or “I’m supposed to be making the world a better place.” Here are some more of the ones I live with: I should lose weight. I’m supposed to be doing more with my life. I should make some more money. I’m supposed to be a good son to my parents. I...

Quality Problems are Real Problems

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I’m not sure where I picked up the phrase “quality problem”, but I’ve been using it recently to describe the doldrums I have found myself in. I’ve written previously about the not-so-helpful habit of comparing my “quality” problems to other people’s “real” problems. Like some prior advice to myself, I’m going to “stop...

How to Celebrate Your Success and Vanquish Guilt

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Here’s a powerful tool that I’ve created to help myself deal with some of my feelings lately around success and guilt. The point of it is to bring clarity in, and get out of the amorphous haze of letting the emotions run roughshod over you when they’re simply not even true and certainly not deserved. This has been modeled on previous tools I’ve created, except this time focused on the particular...

Success Guilt vs Imposter Syndrome

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As someone who suffered from crippling imposter syndrome for many years (and eventually overcame it and even wrote a book about it), I am very familiar with the feelings of being a fake, of thinking someone is going to find out the truth, and everything I have is at risk. There can be no expansion without contraction, and those years of contraction, no matter how painful, were an essential part...

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