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The Secrets of a Successful Entrepreneur

“To dwell in the here and now does not mean you never think about the past or responsibly plan for the future. The idea is simply not to allow yourself to get lost in regrets about the past or worries about the future.” 

– Thich Nhat Hanh, The Art of Power

When we face the unknowns ahead of us, fear can creep up to the forefront of our experience, and direct our imagination into the realm of anxieties. As entrepreneurs, we know this grab bag of anxieties all too well: the restlessness, working long hours to stay ahead of things, sleepless nights, and feeling like you don’t know what you don’t know and can’t learn fast enough to avoid potential failure (as if knowledge-in-and-of-itself really protected us). It’s hard to know which way to go, what to say, or who to listen to. Knowing where you are, and having a clear connection to all the knowing available to you when you’re calm, can give you the clarity you need to navigate from a place more expansive than the contraction of fear.

Shizu Okusa, Founder & CEO of Wellthy & Co, notes in this podcast conversation that “the pull of the shoulds from the past tug at the anxieties of the future.” She, of course, is in the middle there, feeling the tug and pull from each side. This can happen to many of us, in any myriad of ways. Some of us fall prey to imposter syndrome at this juncture. Sometimes, we simply have a hard time knowing which way to go. Sometimes, we are not sure how to appease both tug and pull via our obligation and guilt. 

Fear can trap us from being our fullest self in no shortage of ways. Like, that thing we can sometimes do where we can get caught up mitigating things that haven’t happened yet, in response to things we haven’t even done yet (For example, “If I do X, then someone will do Y (like explode). Therefore, I can’t do X. But I want to do X. But what if doing that thing backfires in some way?”) When I begin managing the perceived possibility of someone else’s reaction to something I’ve done, did, or want to do, then I know my past is showing up in my present (and I’m not really grounded in reality). The tangle of that web of anxiety feels like the fly tape that holds me stuck in the fear of losing a sense of safety, love, and belonging from someone/something ‘out there.’ In moments like that, my clarity of self, sovereignty, intention, and action is obfuscated by my fears about what other people will say or do to me if I do the thing I want to do. Or, even, if I be who I am. 

In that move, the proverbial “they” have all the power over me. When I give up my power in this way, I abandon myself. Fear overrides my agency, my own two feet on the ground, and my own seat in the saddle.  I forget that power was mine in the first place. 

We can give up our power in as many ways as we let fear drive us. The good news is: We can take it back whenever we’d like. 

If only we could get it “right,” we think, then maybe we’ll be bulletproof and won’t feel the sting of our stronger emotions when they arise. Maybe then we won’t feel so paralyzed by them, or maybe we’ll be impervious and not feel the turbulence of intense emotions. 

Maybe if we had our shit together we’d get it right. If we read the right books, knew all the… things, mastered our our day-to-day living such that we could do all the things in a day to keep ourselves together: work out, meditate, eat well, work with a sense of purpose, be a good parent and partner and lover, save for retirement, floss, stretch, journal, and drink enough water. It’s hard to have your shit together according to the world out there. It’s easy to feel like we’re flailing and failing if we rail against that bar of, er, perceived superhuman excellence. 

We do want our best life and (hopefully) want to be the best human we can be. The place we lose our foothold and scramble is when we give up the rating scale for our self and our life to the outside world, thereby judging our weight in the world by the likes, hearts, comments, and reactions of others. One can be ruled, in that case, by the fear that without accolades (or doing all the things superhumans do) you are nothing. We have then not only given up our data to an algorithm (if you chart all of this on apps), but we’ve given our power over to someone else, and we suffer tremendously. We live stuck between the shoulds and the anxieties. Tugged and pulled, this way and that, and likely feeling a good dose of ‘not good enough’ — or some flavor of shame — along the way. 

The best and brightest among us know how to take this power back. The best and brightest among us (that’s you!) know that you only momentarily misplace it from time to time. As my mom (the best angel-mom) says to me in those moments when she hears me spinning in my own fear-driven thoughts, “Remember, Ali: The force is with you.” 

What part of us gets hooked on what the outside world thinks? Our wily ego worries about these things, as if our worth is in the hands of something outside of us. Until we unwind deeper inwards do we realize that it’s only when we find safety, love and belonging in ourselves first and foremost, and it’s there, then, that we become rooted to something other than just to the tug and pull of the world. We can move through the world with the presence of ‘a thunder perfect mind’ in accordance with our own heart. (Easier said than done, I’ll admit.) 

Who we are without the ill-placed longing for the baubles that our ego reaches for is the nakedness where the truth of things live, and where we are with the truth of who we are. I am reminded of  Lewis Carroll’s Through the Looking Glass when Alice in Wonderland enters the Woods With No Name. As she enters this forest, she forgets her name and is guided by a deer, who also has no name. As the story goes…

“So they walked on together though the wood, Alice with her arms clasped lovingly round the soft neck of the Fawn, till they came out into another open field, and here the Fawn gave a sudden bound into the air and shook itself free from Alice’s arms. “I’m a Fawn!” it cried out in a voice of delight, “and, dear me! you’re a human child!” A sudden look of alarm came into its beautiful brown eyes, and in another moment it had darted away at full speed.”

For a while, Alice and the fawn had a direct experience of non-ego. This is perhaps one of the most peaceful and loving scenes in either of the books detailing Alice’s adventures in Wonderland. The direct experience of non-ego is also one of the most peaceful and loving scenes we can arrive at for ourselves every once in a while, as a sweet respite from the bizarre and frightening things we experience in our own mental wonderlands. 

“What we wear without realizing it is the ego,” writes Meggan Watterson, author of Mary Magdalene Revealed. “It’s the stories we’ve covered ourselves with or the stories we have used to obscure the truth of who we really are. And the ego is so well-meaning. It’s like the helicopter mom who thinks we need protection and thinks fear will keep us safe. The ego builds up all these layers of why we should be afraid of who we are, or why we should feel shame about who we’ve been.” 

“Don’t let the rules, projections, and expectations of a society that doesn’t see your true image define you,” Watterson cautions us. I’m not sure who else might find an exquisite leadership book inside of her new book on Mary Magdalene, but I sure did. While pouring over each page, it was clear to me that Mary Magdalene was perhaps the first executive coach. If she was still alive, I’d hire her at Reboot stat. 

Bear with me while I muse a bit: If Mary Magdalene was a present-day executive coach, she’d help us upgrade us from our egoic operating system so that we can react differently. “How can you find yourself in the moments where you feel lost, alone, heartbroken, not sure what to do?” she’d ask. I imagine she’d write articles for WIRED and INC titled “The 7 Secrets of a Successful Leader”, and the enumerated points would sound something like these lines from Watterson’s book: 

  1. Learn to see with the eye of the heart.
  2. No one outside of you knows more than you do about you. You do not need to give away any of your power to anyone, ever.
  3. Know your worth. Believe in yourself, in your own voice, in what you know is true, even if the world around you does not confirm this truth for you.
  4. Move from power over to power with.
  5. You can always begin again.
  6. Doing your inner work is the key to freedom. The inner transformation creates the outer transformation.
  7. Love yourself enough to ask for assistance. 

Hers would be a masterclass on leadership that merges the ego and the soul to become more fully human. And, it would directly apply to our entrepreneurial roller coaster rides, and life in general. Her message sounds subversively simple, but is a solid move to have in your quiver to keep you upright and your integrity airtight as you move through life’s weather patterns and external noise. Hers is a quiet move; one that goes unseen by any audience but you. Watterson writes: 

“Sometimes the most loving thing to do doesn’t appear to be the bravest. It’s not about pushing through or overpowering fear. Sometimes we just need to be with where we are terrified. And not ask the terror to leave or change. But dare to become the one who can hold it in a love that didn’t exist before it, a love that grew, and expanded in order to meet it.” 

This is a great alternative to those habits we may have which precipitate in abandoning ourselves and giving away the power that is ours to the clamor of the world outside of us. Instead, when we sit with our fears, hurts, confusions, and at-a-loss-ness, we are able to find a deeper power that is with us, not over us. We can meet ourselves there in those moments. We find solace and our own two feet and a whole lot of love. It’s like a balm for our worried and anxious selves as long as we remember that it’s there, waiting for us.

The secret of a successful entrepreneur is in knowing this maneuver, and returning to it when needed. There is no place where one can be so smart as to evade all of the feelings that life will evoke. There is no level of consciousness that will protect us from those feelings, either. And, no matter how much of your shadow you unpack, there will always be more. You can’t evade (or take a pill for) your humanity. 

Forgetting and returning to what we know, and who we are, is part and parcel of the human experience just as much as experiencing the wide range of feelings (pleasant ones and plenty of unpleasant ones) available to us. How we include the fullness of our humanity bolsters our wholeness (and I’d argue, our connection to joy through it all). 

“The choice we have, the opportunity that’s presented to us in those moments of exquisite pain, is to also remember the soul,” notes Watterson. “We can bring in the other half of what it means to be human. Not right away, or at least not at first. We can just let it sit on our shoulder or in our back pocket. And even that little presence of light might help us move through the pain differently than we had before. […] Try not to curse the pain, or avoid it. Or to feel like a failure because of it. Try not to run from it, and numb it. Try to see it as our chance to reach a love that can withstand it. Not permanently; nothing is permanent. Just in this moment. That’s all that matters. Find the presence of love in those moments when before you had abandoned yourself.” 

Then, even in the darkest moments of doubt or angst, or even on the eve of the toughest conversations with the most challenging personalities, you can find grounding in yourself. The shoulds of the past and the anxieties of the future aren’t as loud in that place because your own voice will be louder, more clear. That’s a rich moment.

“If you miss the present moment,” Thich Nhat Hanh reminds us, “you miss your appointment with life. It’s so clear.” 

Underneath the ego, and the ways you get hooked at evaluating, judging, and rating yourself, who are you? Who you are under the layers of internalized messages from your culture, lineage, family system, early history, the roles you’ve assumed, the titles next to your name, and the outfits you don? What are the masks you wear to face the world? When you take them all off, what do you find? 

I hope you find the strength of you. The same fiery strength that allowed Joan of Arc to declare: “I am not afraid. I was born to do this.” This strength comes from an integrity that is aligned first and foremost with your heart. It’s as close as your breath (or, maybe three deep ones).


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