The Entrepreneurial Highway

I had an interesting Escape from Cubicle Nation moment this past week: I got a job offer — for the precise type of work I used to do (and love).

The job paid what I used to make in NYC (which would be an extremely nice income in Central Texas), and it was the opportunity that I had been hoping and searching for a year and a half ago.

And the interesting thing that happened?

As I had the conversation, it slowly dawned on me that I wasn’t even remotely tempted.  I’m not sure who was more surprised by this: me or my husband.

This got me thinking about the employee-to-entrepreneur transition that I’ve been on since 2008. We often talk about a “career path.” I think this is inaccurate. I think the right phrase is a “career highway.”

Right Lane = Stability-Motivated Employee

• One career and as few employers as possible.
• Stability reigns supreme.
• Even calculated risks are uncomfortable.
• Large enterprises and government positions often appeal most to this category.
• A single employer career with a stable retirment plan and reliable benefits is the Holy Grail, and boredom is acceptable at work in exchange for stability.
• Any necessary excitement can be sought outside of work when needed.
• “Progress” is most frequently measured in proximity to retirement, more than rungs climbed up a career ladder.

Second Lane = Migratory Employee

• The modern normal.
• An employee who will have 2-4 careers in a lifetime, and an average of 12-15 different jobs.
• Stability is important, but not above all else.
• Calculated career risks are worthwhile, if not occassionally exciting.
• Jumping to a new job is always a possibility if a more appealing opportunity presents itself.
• This employee is often heavily motivated by autonomy and new challenge, secondarily by money.

Center Lane = Freelancer

• The newest class of employee, often placing a premium on freedom and flexibility above stability.
• Often easily bored, and prefering variety with risk to stability with stagnation.
• Commonly enjoys being a solo entity, and is disinclined towards growing a business that requires taking on the responsibilities of having employees.
• Collaboration with other freelancers is often a successful and preferential model.
• “Dollars for hours” is the most common financial model, which can cause business development challenges.

Fourth Lane = Self-Employed

• Small businesses, often family or small-team owned/managed.
• Frequently limited in scalability.
• Often heavily reliant on founder(s) for success.
• Lifestyle businesses and brick-and-mortar neighborhood businesses often fall into this category.
• Not uncommon for an owner to discover that they ‘own a job’ rather than ‘own a business.’
• Freedom and wealth-building often started out as core priorities; over time, the realities of business limitations can undermine those objectives if this was not the intended final growth state of the business.

Left Lane = Business Owner

• Scalable businesses of all sizes.
• Owner/founder has decentralized systems, processes and critical knowledge enough to allow for empowerment and delegation among staff.
• Vacations and sick days for the founder are possible and cause little in the way of organizational chaos.
• This business is a strong candidate for potential sale, since success is not wholly dependent on the original founder for success.
• Owners/founders who build this type of business can/do often build more than one over the course of their lifetime.

Obviously this isn’t an entirely clean mapping, and different combinations can blend a bit to create a bit of a hybrid. But I think that the most meaningful part of the highway metaphor is the idea that people can change lanes over time. Different life factors can influence which lane someone chooses.

• I have seen dozens of female Second Laners have children, and then suddenly switch into either Right or Center Laners (depending on both their personality and their skillset).
• I have watched numerous Second Laners get laid off and decide to take on an entrepreneurial opportunity by moving immediately to the Center Lane, sometimes working their way farther over as time goes by.

This has been my path. I was an obsessive, workaholic Second Laner who was finding a ton of meaning and fun in the career that served me well, paid me nicely, stroked my ego constantly and took me on great professional adventures for a decade. When I hopped off the highway to move to a new town, I (arrogantly) assumed that I’d be able to just hop onto the new road in my new town without any trouble, and slide right back into the Second Lane again.

Unfortunately, my timing was less than perfect. I left my job without a definitive replacement at the same time that the economy took a nose-dive, and before I knew it, my husband and I were starting our own business. It wasn’t the plan, and it wasn’t what I wanted. And yet, that was the course I set out on… and before I even realized it, it slowly became what I truly did want. It just took nearly a year for me to realize that.

And so now, here we are, with a consulting practice and a new Education 2.0 startup business. We don’t have the big salaries or the cozy corporate benefit package and fringe benefits. But we’re doing what we want. We’re working with whom we want. We’re focusing on things that are meaningful to us. And it was nice to get a reminder last week that, no matter how hard it can be at times, I wouldn’t trade it in on the alternative.

So, how did I celebrate? I promptly went a little nuts, cut off all my hair and bleached it blond. A friend and entrepreneur joked with me later, “Is that your way of validating that you aren’t going back to a corporate job?” I grinned. “You got it!” No size paycheck could possibly compare to that.