On Bold Entrepreneurship (and Living!): Notes on Taking the Plunge

by Jill Foster on August 28, 2009

Is there something you’ve been wanting to do?
…like start a business or change your focus? Recently, I was at a cocktail party talking with a woman about her job. She seemed genuinely upset about how her life was going and wanted to change direction but seemed stymied about making any changes. We then talked about my new ventures – quitting my job, launching a new company with two products in the works, trying to consult and doing photography on the side all while writing a book.

“But how?” she asked. My answer – I just did. I got tired of waiting around for the life I wanted to just show up and announce itself.

Assert the moment vs wait
My biggest point to her was that there will never be an invitation or a perfect moment. No one is going to invite you to start in on your dreams – so invite yourself. My “invitation” was that I didn’t like how my company was run anymore and wanted to create an organization I believed in.

I used my savings, downsized my living space and feel confident that if I need more funds to do the projects I love, I’ll find them.

The truth is that we all have abilities that can help others and make the short term cash we need. All of my skills in product strategy, product marketing, photography, writing and more are valuable and I love doing them – why not make them work for me under my own terms?

I went on to explain that it’s early yet
And there’s no guarantee that all of my financial goals and expectations will come to fruition. But so far, there are a few things I’ve learned by being bold – things that make me know, in that deepest way of knowing, that I’m on the right track.

Benefits I’ve enjoyed from acting bold:

On conquering fears (result: a new work identity)
I conquered a major fear – one that is difficult to explain to anyone who has not felt in some part, defined by their work. I had been at AOL for almost 13 years and as a friend once said – that’s like 50 years in Internet time. I essentially grew up there and received more of an education about product development, community management and working with teams then I ever could have imagined. Leaving was terrifying – who would I be? Would I become less important or forgotten about?

And how would I answer that most prevalent question “What do you do”?

While there may have been some moments of uncertainty, I now feel confident and secure about my identity and value as an individual, and that confidence is here to stay.

On designing your life (result: my dream mobile office)
For years I had dreamed and talked about figuring out a way to live more of a nomadic lifestyle – with the freedom to work from anywhere. Suddenly, I realized that with my laptop, iPhone and trusty backpack, I was a self-sufficient mobile office! In the last few months I’ve worked from my home in the DC area, Maine, Chicago, Milwaukee, San Francisco, New York and even Taipei. I’ve worked on trains, buses, airport floors, coffee shops, hotel lobbies and friends’ tables.

Most glorious to me, I often work outside.

Strange as it may sound, it’s quite possible that years went by when the only real daylight my body experienced was the brief walk between buildings on the AOL campus. It is amazing how good it feels to work outside. I know that I am productive, responsible and creative no matter where I am working and will work hard to ensure this freedom lasts.

On growing (result: my self-promotion and social skills improved)
While there are opportunities for personal growth while working at big companies, being on my own has pushed me to grow in new ways and offered opportunities for growth in some very unexpected ones – and this is just the start! My social skills have improved, confidence and self-promotion included. Creatively, I’ve been able to stretch and surprise myself with things I didn’t know were in me (I can cook!). Most importantly, I know my enthusiasm for self-growth has deepened and I do not fear failure. Failures will happen, but they are part of the journey and since I write my own annual review now, I vow to give myself a gold star for every failure moving forward – because failures mean I’ve tried, reached, extended myself and learned. Bravo.

On living in the now (result: I finally chose to be an entrepreneur)
I know that I’m no longer putting off ’till tomorrow what I can do today. All my life I’ve talked about living a life less ordinary and being an entrepreneur. But it was always a future dream. But there is no future – there is only now, and I finally learned that lesson. The words sound trite, but when you finally understand it, feel it and know it in your gut, waiting is no longer an option.

On being a witness (result: my environment motivates my decision)
The deep knowing I mentioned previously is echoed and reinforced everyday. When I am open to it, synchronicity appears – not just in little ways, but in giant, loud, billboard screaming ways. Now that I think about it, that might be the most fun of all! Witnessing the world around you as it organizes and rallies to propel you to where you want to be.

So, as my friend and I chatted at this party, my basic message to her was this – be bold.

There are no rules to how you have to live and if you can just let go of the messages and fears that have been deeply programmed into our psyches telling us to fear change and that we need our “steady” jobs with half-walls, formica desks and 9-5 schedules, titles and annual reviews, we’ll finally know that those dusty dreams in the attics of our minds are not only possible, but highly plausible and we are doing the world a disservice when we ignore them.

Boldness has genius, power, and magic
About two-three months ago, I found myself in the midst of a highly creative phase (which happens quite a bit more these days) and an idea struck me. I have a book in me – many in fact, but one that is meant for now. And not only would I start writing it asap, but I would announce it on my blog along with a photo contest inviting others to be a part of it. After I announced it, doubt flooded my mind – can I really do that? What will people think? Will people say bad things? Will anyone buy it? Who am I to make such a bold announcement?

And that’s when I remembered.
For almost 13 years I kept a Goethe quote with me that resonated but apparently took it’s time to penetrate. “Whatever you can do, or dream you can, begin it. Boldness has genius, power, and magic in it.”

As complete strangers sent me emails and entered my contest, I witnessed the magic. As photographers I deeply admired and felt were out of my league offered to help, I felt the power. Now I show up everyday and put the work in – and remain hopeful that some greater force will infuse a bit of genius in there as well.

As I mentioned, it’s early yet. Who am I to say follow your bliss?
Who am I to give advice about designing your own life? Honestly, I’m just someone who dug deep and remembered Goethe. I also trust myself – shouldn’t we all? If you are happy in your current environment, great! If not, dust off your hidden dreams and bring them out into the bold light where they belong.


Guest contributor Jen Consalvo writes the Women Grow Business series on all things related to launching product (pre and post launch). She is co-founder of Shiny Heart Ventures, a new technology startup focused on building community driven products that remind people of the joys of life. For almost 14 years, Jen has led teams in a range of product areas such as digital imaging, social platforms and personalization. The majority of her career was at AOL, planning and building products used by millions of people globally. Also find Jen at jenconsalvo.com, bodysoulconnect.com and twitter.com/noreaster.

(Image Taipei 101 and Kite, by guest blogger Jen Consalvo, used with permission)

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