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Entrepreneurial Reflections

All of us are part rebels; for some, it's the significant portion.  At an early age, some realize a crucial truth "You can't make me." Later, confronted by a micro-manager, they might think, "You are not the boss of me."[1]

Rebels are driven to express their identity authentically and are inspired by personal freedom and challenge. A sure way to motivate rebels is to imply they're not up to the task. Understandably, most managers prefer that we keep doing what we're already doing well, which can stifle the moderate rebel. Since rebels resist external direction, they often gravitate to entrepreneurial careers. However, they can thrive in organizations that provide the right environment.

But rebels have their fair share of contradictions. While they generally do whatever they want, they may sometimes resist even their own decisions. On the other hand, they may serve someone they respect with devotion. Like all personality types, people identifying as rebels are a mix that may include being 'obligers.' Whereas people are mainly predictable, we're able to transcend our personalities.

I'm convinced everyone has unique gifts and powerful forces driving them, but developing and articulating them takes time. It is hard to know ourselves; the acid test is, do you see yourself as those who know you well see you? 

In retrospect, I can see how my mission was not something I could have described a decade ago but has sharpened into something I can speak passionately of now. Circumstances and other people have provided the battleground that revealed my innate tendencies. I once had a boss who deemed my work good enough and, therefore, complete, whereas I considered it ugly and worked on it covertly until it was acceptable to me. In another role, I was convinced that a solution to a particular problem existed, whereas my superior did not and told me to drop it - more than once. Undercover, I emerged a few weeks later with my ground-breaking solution. These recollections provide insight into my character: I want to build a reputation for excellence. I'm an inventor who appreciates beauty, am not easily dissuaded once convinced, and am a tenacious implementer/finisher willing to go it alone if necessary. While I'm happy to lead by example, there are limits to how far I would urge a reluctant team. I am a helper/enabler who cares for and develops my team, but it's on my terms.

Research shows we all need small wins to be happy at work. The most rewarding firms to work for will have top-notch leaders and opportunities for growth. Small firms are best for developing the broad experience to strike it out alone and are less likely to have confining rules and procedures. Startups are rocket ships - so don't ask which seat you'll be assigned. Prefer organizations in which you can imagine yourself having a future.

Hierarchical organizations have an inherent problem; if each of us has aspects of work we love and areas we struggle in[2], does it make sense for staff to pay their dues (doing what we're not good at until we get promoted - or fired) - or conversely to be promoted to a role we won't thrive in? On the other hand, flat team-oriented organizations group diverse people so that together they function as a unit able to handle all aspects of their collective tasks.

Different forms of employment (employee, contractor, freelancer, entrepreneur) have advantages and disadvantages. Whereas contracting got me an excellent hourly rate, going it alone has been the least financially rewarding so far. Becoming a maker/entrepreneur gave me ultimate control over my work but entailed massive investments of unpaid time.

There is a dichotomy in one's choice of product or service. If it's a new thing, you'll have a free hand but must develop the market - only pre-early adopters evaluate new products on merit alone. Pick an established market and reduce risks considerably, but expect to be squeezed by the incumbents. Don't underestimate the number of sales 'touches' needed to build sufficient trust, and understand that prospects enter the buying window in their own time for reasons beyond your control. Selling an Enterprise SaaS (Software as a Service) product like Cloud49 costing $1000+/month can take months of skilled sales activity with multiple decision makers for a single sale[3].

Going solo entailed educating myself about business, leadership, marketing, and sales. I instinctively understood I had to earn the respect of myself, my colleagues, and my prospects, so I signed up for sports events and got physically fit. I started getting active on LinkedIn, blogging, and building marketing websites for my products. Logically it seemed that if I kept improving my skills, credibility, and creations, I'd break through at some point. Well, at the least, I would be better equipped to join someone else's startup.

Training myself for leadership affects all areas of my life. Experience only comes with time, but walking a path of balance in all choices while eschewing the pursuit of happiness is the way.


1. Book: The Four Tendencies by Gretchen Rubin
2. Book: The Six Types of Working Genius by Patrick Lencioni
3. Website: https://about.crunchbase.com/blog/saas-sales


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