Today in Female Empowerment: BOUNDARIES

The part of me that tends to be an over-promiser and under-deliverer is learning, painfully, that change is afoot.

I like to please people. I never want to disappoint people. I’ve always wanted people to like me: I’ve been thirsty for that feedback like a vampire is thirsty for blood.

My value--I’m a good person, dammit!--has been tied up in how other people see me, presumably because the alternative would make me feel abandoned or unwanted. A big part of that is what I want to do for them, or at least what I hope and promise to do for them.

What I actually CAN and WILL do for them is another story. Ironically, not wanting to disappoint people has led me to do none other than...disappoint people.

When we were raising money to start my former company Uplift, I twisted myself into a 1970’s yogi to make good on my promise to my then co-founders that people I knew and were my contacts were actually going to invest after we did our first round of fundraising because as it turned out, starting a business is expensive and that round had come up a bit short. (Never mind the fact that I’d already brought people to the table who’d invested, not to mention conceived of the entire business and brought all of our clients to the table. Even with that, I still felt like I wasn’t measuring up and had to do more).

So that led me to:

A close family friend who has a lot of money was wowed by my pitch, promptly committed, stayed in touch, and then simply never followed through with the actual check.

A friend from my university days who expressed interest in investing (our previously completed round had included other friends from the same circle), and then showed up to the meeting with me and my co-founders actually stoned, and worse, flippant, about our business and women-owned businesses in general.

And then there was the man who, after we’d met at a business lunch through another investor, also promised and promised he was going to invest. Game-changing, business-scaling money. He said he wanted to meet with me (and only me!) to discuss the investment. The meeting was at night, at a bar. Yes, I was hopeful and naive, or maybe even willfully blind. He kissed me in short order. Before he could Harvey Weinstein me up to his hotel room, I found out he was married (no ring, of course) and hightailed it out of there. The next day he called and coldly informed me he wasn’t going to invest anymore.

My burning desire to bring something to the table put me in humiliating, weird, and precarious positions, all because I couldn’t bear to simply say to my co-founders, “This person isn’t the right fit for us as an investor.”

As I think through all of those past experiences, the ever-evolving me  is digging into the idea of boundaries. Learning about them, and starting to learn them well.

My Pillars of Female Empowerment start in cluster #1, Clarity, and having that as an anchor has helped me start the climb up the ladder of empowerment into cluster #2 (Connection), straight into cluster #3, Consciousness-Raising, where the Pillar Boundaries lives.

I know now in any given circumstance that I need to ask myself, with whatever I am thinking about, is this right for ME? Is this going to make ME content, stable, and calm? Is this going to be something that benefits ME, helps me grow, and makes me a better person?

Looking back, none of the three potential investors I mentioned before would’ve actually been good for the business for a variety of reasons, and they especially wouldn’t have been good people for ME to be involved with long term.


Having (or not having, as it were) boundaries forces a person to take a long look at herself and think about the question: Who am I?

This applies to every single area of life. Take dating. I know so many of us date someone with the thoughts swirling: Does he like me? Is he going to call me? Will he think I’m crazy because I like going to bed at 8pm? Is he going to fall in love with and marry me next week?

My embrace of boundaries has turned that on its ear. Now, I look at every guy I date thinking, Do I even like you? What will you add to MY life? Do you make me a better person? What do YOU bring to the table?

Even my family--whom I adore and love and spend so much time with--wanted to do a weeklong vacation on the Jersey shore this coming summer. I honestly just sort of didn’t: I’m single and ready to mingle and would rather spend my vacation time and money tacking some days onto the trip I am taking to Europe this summer for a wedding. But I hemmed and hawed because I didn’t want to admit the truth to them. I almost reached the point of committing to the house, which would’ve inevitably caused me to feel at least some resentment. Luckily my family knows me almost better than myself, could sense my reluctance, and nudged me into a graceful bow-out.

(And now, of course, I’m having FOMO and am definitely going to visit the shore house the week they’re there!).


I’ve realized that Boundaries were even at the heart of closing Uplift. I was working like a dog literally only for my investors and for my former co-founders, who’d walked away from the business years before but still had almost as much equity as I did. I was barely paying myself a living wage, and was killing myself to keep us going but at the same time losing so much heart and inspiration and motivation because I could see the writing on the wall. I kept us open far longer than I should’ve because I didn’t want to disappoint people - clients and colleagues.

And you know what? I DID disappoint people. A LOT of people.

In closing that business, though, for the first time in a very very very long time, I chose myself.

Getting over the socialized idea of how selfish that is was tough, but in the end, one of the most empowering decisions I’ve ever made.

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