I don’t journal daily but moving surfaced a stack of notebooks filled with entries from my mid twenties until now. Last weekend, I flipped through an old notebook and saw that I kept referring to this idea of writing a letter to a random journal entry. And then on Monday, I started reading Stacey Abrams’s book Lead from the Outside. In the preface she talks about how she questioned writing the book at all, doubting if people would be interested in her story until she met a stranger who embraced her with a hug once day for being forthright and showing her a reality that she didn't think was possible or probable. I started thinking that maybe what I’ve learned from my past could be helpful to someone.

I’ve wanted to try this for some time but kept talking myself out of actually hitting publish for months. I had so many excuses: lack of time, too much travel, concern about quality, worries about how it would be received. Every time i thought about clicking publish my stomach turns at making my innermost thoughts digital. But here we are because I realized all of those excuses were crap. I wasn’t writing because I wasn’t writing…by choice. Whatever fears I had were neither fully formed nor truly terrifying. I simply ran out of reasons to procrastinate.

So I’ve typed a random journal entry from August 2015 with the intention of responding to it with the perspective and advice I wish I had known at the time.

August 17, 2015

It’s been a while since I’ve journaled and a lot has happened. This last weekend has really been great for getting me out of my head and putting things in context.

Thinking small has made me both fearful and my worst enemy. I rewatched the Brene Brown TED talks which really put things in a new light. I’m scared of being success and i’m sure it’s related to not feeling worthy and deserving of it. It’s the same reason I get so anxious about my relationship.

The only way to overcome this fear of vulnerability and worthiness is to be exposed and open. I need to vocalize my wishes and desires because after all who gon stop me? Certainly not me.

In the car last night, N*** started talking about how he wished that he had become an entrepreneur sooner. He was always finding new ways to solve problems and feeling stifled by bureaucracy which has been my experience. I need to talk to him about making that shift. I really want him to mentor me.

This has really shown me the time for action is now. I have three business running in parallel.

I am entrepreneurial. I am an entrepreneur.

It’s time for me to claim that vision and fearless work toward it. The courage is in the effort and persistence, not the outcome.

I won’t say I don’t know because I know what I want. I don’t know is a symbol of doubt and that has no place in my vision.

My vision is full of creativity, love, beauty and financial prosperity. It’s mine for the taking.

Dear Vanessa of August 17, 2015,

You were really scared when you wrote this. Four months prior you quit a job that one could say (diplomatically of course) did not serve you or your purpose. You took a risk on yourself in ways that you hadn’t done since deciding to move to Mozambique in 2007. Your anxiety is at an all-time high as you try this new identity: entrepreneur. Which is interesting to say try because this is not the first time for you. Nevertheless, you feel the full weight of your decision as well as the burden of your anxiety judging yourself.

So you try these affirmations that people keep raving about: positive statements about worth and purpose. But it falls flat before the ink even dries on the page. You don’t even touch this journal for two more months when external circumstances have changed even if your mindset hasn’t.

Nevertheless, you see a glimmer of your true self in engaging in the exercise of daring to write that you deserve to be in that creative entrepreneurial space rather than disinviting yourself. Shutting down yourself is an express train to disappointment and dissatisfaction. You also see this self-reflection and self-sabotage for what it is: fear of success obscuring doubt of self-worth.

So you spread yourself too thin, working on three businesses rather than the one that you really want. You think that you are choosing and pursuing what you want when really your fear and anxiety make you work overtime to cover your bases. And although you write about vision and imagining this future, you’re afraid of what the next week, next month, and next quarter hold for you as financial tenuousness becomes entangled in larger-than-life anxiety.

In retrospect, it’s not the best step but it’s the step that you needed to take to believe that you were capable Without the glimmer of affirmation and validation, you would not have put yourself out there. Thinking small could have made you play small; instead you saved yourself from yourself. No parents, no boss, no mentor…just you letting yourself be yourself.

So even though the outcome you wanted to happen didn’t, the outcome that needed to happen did.

Fighting yourself is a lifelong battle only if you keep up the resistance. Now you know if you feel groundless doubt and that churn in your stomach that the physical fear response and the raging doubt are all smoke and mirrors.

So do what you want and not merely what you are expected to want. And bring Tums for that anxiety nausea.

Vanessa of August 28, 2019

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