Category Archives: Work Life

The Road to Gainful Self-Employment

be your own bossA few years ago, Pew Research conducted a study to determine the size of America’s self-employed workforce. They found that 10% of the active workforce – or 14.6 million people – were self-employed. As these individuals employed another 29.4 million people, they accounted for roughly 30% of the workforce.

I’ve counted myself among their ranks for over a quarter century. I never set out to be self-employed. It just turned out that an active consulting practice afforded me some freedom alongside the opportunity to do interesting work with bright people. That freedom comes at a cost:

  • Work has never just fallen into my lap. I’ve always had to work at getting work.
  • I’ve had to wear a lot of hats to keep the business going above and beyond doing the actual work – e.g., business development (a.k.a. marketing and sales), client relations, billing, collections, accounting, and general administration.
  • I’ve needed to price my services to account for all of those roles as well as holidays, vacation, sick time, personal days, and saving for retirement.
  • I’ve had to purchase individual health insurance… which isn’t cheap!
  • I’ve had to learn to manage my time effectively from my home office to make sure household responsibilities do not spill too much into business and vice versa.
  • I’ve needed to learn how to cultivate community as part and parcel of my sole proprietorship to keep the extrovert within me satisfied.

Despite the challenges, I’d still opt for working for myself if I had it to do all over again. And as I plan for the next chapter of my life, I’m still thinking about ways in which I can work for myself.

I just finished reading Chris Guillebeau’s book Side Hustle: From Idea to Income in 27 Days. It proceeds from the assumption that folks would like to make a little money on the side while they continue to work their day jobs. These ventures might exercise their creativity while adding a little cash to the household’s bottom line. They might be used to diversify income sources. And they might be the initial stepping stone to going “all in” as an entrepreneur.

Chris does a great job of breaking down the entrepreneurial process into discrete steps that pretty much anyone can follow. His 27-day process covers:

  1. Building an arsenal of ideas
  2. Selecting your best idea
  3. Preparing for lift off
  4. Launching your idea to the right people
  5. Tracking progress and determining next steps

Even with my MBA and decades of business experience, I found some pointers in Chris’ book that I’ll put to use as I contemplate my next venture.

Another great resource if you’re considering this path is Jonathan Field’s Career Renegade: How To Make a Great Living Doing What You Love. Jonathan is the Founder of the Good Life Project and hosts a lively podcast by the same name. He endeavors to help his readers find work that makes them come alive while also paying the bills. He provides all kinds of suggestions for finding underserved markets in which one might establish a toehold and build a successful business. The book also comes with a gaggle of concrete suggestions and resources that help readers go from wishful thinking to reality.

The Progress Principle

I’ve come across a number of studies in the past few years that link employee satisfaction with their productivity and tenure on the job. Not surprisingly, when people are happy, they do better work, they enjoy the work they do, and they feel good about the company and co-workers. So the $64,000 question becomes: How do you create an environment that fosters these sensibilities? Dr. Teresa Amabile, PhD and Dr. Steven Kramer, PhD share their insights in The Progress Principle: Using Small Wins to Ignite Joy, Engagement, and Creativity at Work.

the progress principleTalented employees look for their employers to provide meaningful work, clear goals, and appropriate measures of autonomy, resources, and help. The degree to which the company delivers on these key elements of their work life affects their creativity, productivity, commitment, and collegiality. Moreover, companies add “booster rockets” to performance by creating opportunities for employees to realize small “wins” on a consistent basis. Progress stokes motivation.

Most managers aren’t clued into the importance of progress. They rest too easily on compensation packages, longer term performance incentives, high-level goal-setting, and recognition. Yet progress confers confidence and a sense of empowerment. It creates and sustains momentum. Amabile and Kramer would argue that work plans with many small milestones prove more effective than those with a handful of big ones.

Beyond architecting projects with progress in mind, the following factors contribute to an atmosphere of positivity:

  • Due consideration for people and their ideas
  • Adequate time to complete the work (but not too much!)
  • Clear, honest, respectful, free-flowing communication
  • Encouragement to overcome stumbling blocks and forge ahead
  • Post mortems on problems and setbacks that foster learning in a context of psychological safety

Attentive managers stay in touch with their teams to be mindful of their progress and needs. They “check in” without making folks feel as though they’re “checking up.”

As a former corporate employee, I certainly resonated with the core messages in this book and valued the research used to back it up. Yet as one who has been self-employed for many, many years, I needed to adapt the findings to account for wearing the employer and employee hats simultaneously. The obvious adjustments will surround my weekly “to do” lists, as follows:

  • Build each week’s “to do” list with enough work to keep me occupied without overloading the plate (and, therefore, making me feel discouraged or put upon)
  • Define tasks in greater detail to give more opportunities for victory celebrations
  • Reflect on what I’ve accomplished at week’s end rather than simply moving on to the next set of projects and chores
  • Enlist support and resources to help make progress faster!

The “It” Factor in Start-Up Enterprises

Early in my career, I had the opportunity to work for a venture-funded start-up called Octel Communications. I’ve never worked so hard nor had more fun on the job as in those early days of the company’s history. So when I picked up Randy Komisar’s NY Times best-selling book – The Monk and the Riddle: The Art of Creating a Life While Making a Living – it felt like old home week.

entrepreneurKomisar was a successful entrepreneur who became a venture capitalist in 2005. His book follows the travails of would-be entrepreneurs as they work with Komisar to secure funding for their businesses. He starts with three fundamental questions that venture capitalists ask when business plans come across their desks:

  • Is the market for the product or service large enough to warrant investment?
  • Does the business plan outline the means through which this company can become the market leader?
  • Do the entrepreneurs have the knowledge, skills, experience, resources, connections, et al to execute the plan?

That being said, most MBAs have adequate training to craft business plans that address these issues. Astute venture capitalists look for something more – an “it” factor that transforms a good idea into a great company. As Komisar explains:

“Don’t confuse drive and passion. Drive pushes you forward. It’s a duty, an obligation. Passion pulls you. It’s the sense of connection you feel when the work you do expresses who you are. Only passion will get you through the tough times.”

“The chance to work on a big idea is a powerful reason for people to be passionate and committed… For people to be great, to accomplish the impossible, they need inspiration more than financial incentive.”

“Set the compass, then work hard to clear a path, knowing that you may meander as you stumble upon obstacles but will always keep heading toward the same coordinates.”

Citing his own company and business partner as an example: “Bill had an underlying faith that if we focused on the people issues, worked hard, and did a great job, the business would take care of itself… [Our customers] valued our products. Our partners respected and trusted us. Our employees were highly motivated and committed… There was an intense sense of loyalty and camaraderie.”

“Excellence is not simply the spoils that come with good fortune. It should be the primary measure of success.”

Komisar ends the book by asking his readers if they’re doing what they truly care about. He opted for a distinctive life journey that reflected his ideals and values. As he says:

“What was the sense of rushing down a beaten path with a map that I had cribbed from others? This was my trip, my life, and I needed my own journey. I decided to throw away the itinerary and see where this might lead.”

In case you’re wondering, Komisar offers up the back story for the intriguing title to his book. While it’s easy to paraphrase, I’d rather give you one more reason to check out the book yourself. It’s a worthwhile read.

Coping with Uncertainty

As the 2011 winner of 800-CEO-READ’s best in category for personal development, Jonathan Field’s Uncertainty: Turning Fear and Doubt into Fuel for Brilliance grabbed my attention. I’d been listening to his Good Life Project podcasts and enjoyed the content. I’d also read his 2016 book How to Live a Good Life. So even though I wasn’t looking for entrepreneurial advice, I figured he’d have something interesting to say.

uncertaintyFields asserts that creativity and a tolerance for ambiguity go hand-in-hand. When attempting to bring something entirely new into being, the initial concept may or may not work. You may or may not build the team or acquire the resources to reach the finish line. The market may or may not rally around the product or service. Yet Field’s core message is: “The more you’re able to tolerate ambiguity and lean into the unknown, the more likely you’ll be able to dance with it long enough to come up with better solutions, ideas, and creations.”

While I’m not hankering to bring the “next big thing” to market, I’m standing at the crossroads of the next chapter in my life. I understand the temptation to lock in on a safe course to ease my anxiety about what comes next. Fields suggests that I build some “risk, exposure, and uncertainty scaffolding” to give me an extra boost of calm as I move forward. Here are his suggestions:

Build and practice daily rituals that accord with the ebbs and flows of energy throughout the day. He deems such practices the “psychic bedrock” that keeps you grounded and productive even when you feel anxious or simply don’t want to get down to business. It defends against the urge to procrastinate. And when supported by your natural biorhythms, you take full advantage of your peak hours of productivity.

Intersperse bursts of creativity and productivity with rest periods. As Dr. Baba Shiv of the Stanford Graduate School of Business discovered, willpower gets depleted via heavy thinking, working memory, concentration, and creativity. Our brains need to re-fuel periodically to function properly. Forty-five to ninety minutes of work followed by light exercise, a short walk, meditation, a cat nap, or the like should do the trick.

Find a mentor or a champion to provide support and encouragement on your journey. His or her advice and confidence can be an antidote to unfavorable internal or external judgment. If the right person has not surfaced, find and study a hero whose journey inspires you.

Learn to pivot. Be willing to make and own mistakes. Give yourself permission to course correct if the available evidence, constructive feedback, and/or your “gut” instincts suggest a new direction.

Engage in attention training – e.g., meditation, mindfulness, or other contemplation-driven spiritual practice. Fields notes: “Through daily repetition, they create both physiological and psychological changes that can profoundly alter the way we experience and handle nearly any challenge or endeavor… They also open channels to insight and innovation.”

Practice process visualization to gain traction around the steps and actions needed to realize a goal rather than simply the outcome to be achieved. In so doing, you end up engaging in those processes with greater regularity and increase the likelihood that you’ll get to the finish line. (Greatness is largely about work!)

Take care of your body by exercising, eating healthy foods, and getting plenty of rest. Exercise elevates mood while easing anxiety. It’s also correlated positively with brain function. The key to sustained effort is finding activities in which we genuinely find pleasure. While it may seem counterintuitive to take time away from work for self-care, the payback in improved spirits and cognitive function more than compensates for this investment.