As I’ve been reading and rereading the self-help books that will somehow transform my mind and make this entrepreneurial path suddenly easy (yeah right), I’ve had several light bulb moments. Not those big beautiful incandescent globes. No, I’m talking tiny, twinkling gnome-hat bulbs–the kind found draped over shrubberies during the holiday season. Itty bitty shiny realizations.
Realization #1
Many of the blog stories inspiring folks to trade a nine-to-five for their own online business have a lot to do with exotic world travel. Bloggers gush about remote work locations in the Bahamas, and for the first time ever, readers get excited about what’s possible for their lives. These stories are important and very much needed.
Unfortunately, they don’t do a whole lot for me because I’ve traveled my ass off; I’ve been to Europe five times. Five!! I’m not saying that to be boastful. I am fortunate to have a mother who introduced me to international travel at the ripe age of 11. So, I caught the travel bug early and made European backpacking a top priority. When something is a priority, you figure out how to make it happen again and again and again.
But something has changed. My priorities are shifting. And now I’m talking to myself:
Lindsey, why the hell did you quit your job?
Because I was miserable. Duh.
Yeah, but what about it was making you so miserable?
You mean, besides the soul-sucking management practices, prison-like glow of overhead fluorescents and confining cubicle walls?
Yeah, besides that.
Good question. I was miserable because I had the skill and the means to fully empower clients in improving their lives, but was required to hold back and do less for the client due to company constraints.
Imagine Superman forced to ride a public bus to save a woman from a burning building, only to find her already crispy by the time he gets there. That was my level of frustration.
As much as I love the flexibility and freedom of working for myself, it’s the opportunity to do truly meaningful work and better peoples lives to the full extent of my creativity, that drives me. That is my priority now.
Realization #2
The scariest thing about quitting didn’t have to do with loss of income. I didn’t quit that job. I quit traditional employment as a whole. I’ve made a commitment to pursuing self-employment and entrepreneurship for the rest of my life. It’s not that I’ll never have a job again. The fact is I might temporarily need to sustain myself with a part time gig here or there until I figure out how to make money independently, but I will never again rely solely on an HR Department for my economic survival.
Realization #3
I also made a commitment to create a livelihood that’s in harmony with my deepest values: honesty, sincerity, connection, loving-kindness. This seems like a tall order for such a naive and inexperienced entrepreneur. It means I face questions like: “Is there such thing as honest marketing?” and “If not, can I create it and still be successful?”
I’m doing my best to embrace the uncertainty of it all (with a lot of help from the admirable Jonathan Fields). My progress has been somewhat slow, but I have made progress. That’s all I’m counting for right now.


