10 Lessons from 10 Years of Being My Own Boss

Pregame Group Session-3

As of this month, I’ve been my own boss for 10 years. TEN YEARS! I deserve a promotion. It wasn’t my original plan. I was laid off during the recession, and ended up landing freelance clients. In order to start a business bank account, I had to form an LLC, and thus Pressler Collaborative was born. I hate working from home, so I rented an office. (Fun fact: I was […]

Are You Living Your Practice Life or Your Real Life?

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As a life and career coach, I’m supposed to have my shit together. But I don’t. I don’t make enough money to pay my bills. I don’t eat right. I don’t have a life partner. I’ll never be in shape the way I was when I was swimming 4 miles a day. Or when I was training for a marathon. It’s beyond embarrassing to admit this—that I don’t have my […]

Five Steps to Consciously Creeping Your Lifestyle

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Sometime in the past few years a little phrase started to make its way into the vernacular around water coolers and on entrepreneur blogs everywhere. Lifestyle Creep is the term used to describe the phenomenon of spending rising in proportion to income. If your expenses rise at the same rate your income ascends you never feel as though you have extra – it’s already spent. The articles I have read […]

Eyes on the (Real) Prize

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  Sydney, Australia, 1989. So here I was… making it in the super-competitive business world. I was: heir apparent in a major multi-national ad firm, marketing writer, national new-business director, just voted in the top 10 across the country, blah blah. An ‘80’s Mad Man. And then we had a third child, unexpectedly. I came home one night late (as usual) from the office and my wife asked me to […]

Six Things You Can Do Right Now to Move Toward Finding Your Soulmate

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In 2013, I decided to make some significant changes in my life.  I was divorced, working in administrative assistant level positions, doodling on the sides of my notebooks, and wondering where my ambition and passion had gone. What was I doing?! What did I really want in my one, beautiful life? Luckily I had some great friends on the same journey. Asking themselves the same questions. One of those friends […]

The Lonely Ballad of The Someday Guy

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The other day I was having coffee with someone who is in the field of video production and he brought up an interesting question. He asked: “What do you do when you’re meeting people and they keep telling you that they don’t need your service right now, but to send your information because they could use it someday?” He explained how this dynamic was causing his business to have a lot […]

One Step

5. Pieta (Untitled Art Fair 2018)

Lao Tzu famously wrote that the journey of a thousand miles starts with one step, which despite its face value, “yeah, no shit” philosophy, tells me that even the greatest achievements and distances are realized in the smallest of increments, and that paramount to all, is that there is a start. One must simply start, as small a step as it may be, in order to get from here to […]

What If It Really Is All About the Journey (or the Hokey Pokey)?

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I have to be honest. It makes me panic a little when I think life really is all about the journey and not the destination. Because that would mean, if I believed all that Buddhist-mindfulness-meditation-acceptance-is-the-answer logic, I should be able to make myself happy RIGHT NOW. I should find joy in every moment. I should embrace the suck. Pain is a portal. Ugh. The pressure. And, that, my friends is […]

We Are All Entrepreneurs: Being the CEO of You, Inc.

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In today’s culture, entrepreneurship is glorified. But for all the wrong reasons. We elevate founders – well, the conventionally successful ones – to heights previously reserved only for rock bands and movie stars. Success, the ultimate American value, is exemplified by the narrative of the solo dreamer who had an idea and then through grit, determination, and deserved good fortune, achieved fame and material wealth within his lifetime. Of course, […]

What If Money Were Your Lover?

Truong Tran, Fraternal Twins

Ewwww. That thought makes me squirm. I don’t really want to think about my behavior in relationship to money. But admitting my problem is the first step in solving it, right? My relationship with money certainly has evolved and taken many forms. I can tell you that, just like when I was married, I have dragged money to therapy so it can find out how it needs to fix itself. […]