“Choices are the hinges of destiny.”

~ Edwin Markham

“Ever notice that ‘What the hell’ is always the right decision?”

~ Marilyn Monroe

Not always, Marilyn. Many self-employment failures come not from lack of effort or smarts, but from lack of discipline in initially identifying one’s needs and what will meet them. Half the battle in getting what you want is avoiding side streets that have you chasing something you think you want, only to find out that it’s far less satisfying than you expected. Not everyone is able to enjoy what they asked for when they finally get it. (Like Willie Nelson joked, a skeleton walks into a bar and says to the bartender, “Gimme a beer – and a mop.”)

Unless you’re just a skeleton, few decisions are as emotionally charged as choosing how you’re going to spend the majority of your waking hours. But when it comes to this thing called “work,” even the most abstract of considerations can be looked at with more rationality and discipline than you may think. Unless you’re dead certain of exactly what you want to do, and that it’s tightly aligned with your needs, values, priorities, and truth, you will want to evaluate alternatives as methodically as possible. And for some of you, one of those alternatives may be not working independently at all. But we’ll come to that later in this chapter.

Clarifying Your Needs, and What Will Meet Them

When we evaluate any set of alternatives, we need two things before we can start: (1) alternatives that are well enough defined to know what we’re evaluating, and (2) a set of well-defined criteria on which to evaluate them. The pitfalls when trying to get those two things right have revealed themselves over and over in choices made by client companies I’ve advised over the years. As I’ve also seen with my coaching clients, those pitfalls are at least as relevant to us as individuals when choosing the path forward for independent work (or, for that matter, for remaining employed).

In business, strategy is all about making choices, and executives and consultants invest much time and money in analyzing those choices. So in charting your personal path, what can we learn from how disciplined, market-leading companies formulate strategy? Or, for a more concrete example, what can we learn from how they optimize choices when deciding what new product innovations to invest in? Many millions, sometimes billions, of dollars/euros/yuan/yen are at stake in revenue and costs. (Yes, I know – your personal fate is worth more than that! Priceless, in fact.)

When I advise client companies on what new products to make (and not make), and what features and functions those products should have (and not have), I approach that with a patented methodology called Strategic Harmony® that has also been adapted for personal coaching and career coaching. What can we take away from the fact that many more new products fail in the marketplace than succeed? Time and again I’ve found that the majority of product failures can be traced back to one of two causes that precede any mistakes in product design, manufacturing, or pricing. The first is that the company evaluated those products on the wrong criteria, or on criteria that were inadequately defined or poorly prioritized. The second cause is that the definition of the product at the outset was too vague. The result was that each person on the evaluation team either had a different vision of what the product would be, or didn’t understand it clearly enough to really know what they were evaluating.

So what about you? Whether you’re choosing between two or among a handful of alternative scenarios for independent work, or just choosing between one independent scenario and staying at your current company, the same principles apply.

Let’s look at your criteria before delving into your alternative paths. I start with the criteria because you’ll want the evaluation of those alternatives to be guided by the criteria that are most important to your fulfillment, effectiveness, and ultimate success. I call these criteria drivers of satisfaction. Satisfaction with work is a mashup of happiness, purpose, and self-actualization that brings an ongoing sense of meaningfulness and well-being. Independent work or otherwise, purpose-driven work will always be both easier and more satisfying than just working to earn a buck. It matters little whether you call your criteria drivers of satisfaction, drivers of meaning, drivers of joy, or drivers of inner peace. What matters is that you’re very clear on what defines your ideal work experience, so that the path you choose – though it will always have trade-offs and can never optimize all your criteria – can land you in the best possible place.

Adapting Maslow: Your Hierarchy of Work Needs

For those of you not familiar with Maslow’s “Hierarchy of Needs,” Abraham Maslow, the influential 20th-century psychologist, forged groundbreaking theories regarding motivation, personality, and human behavior. His Hierarchy of Needs framework was visually expressed as a pyramid with the most basic human needs for survival (such as food, water, warmth, sleep) at the bottom foundational layer, and “self-actualization” needs at the top (such as creativity and problem-solving). In between were safety needs, the need for love and belonging, and esteem-related needs such as respect and feelings of accomplishment.

In evaluating your options for work or career, you will have a more tightly scoped hierarchy of needs that’s a subset of Maslow’s hierarchy. But there are two highly relevant things about Maslow’s hierarchy that can help you more accurately predict not only whether independent work is really for you but also what that work should (and shouldn’t) be. The first is simply the fact that needs are indeed a hierarchy – a set of desires that are not all equal in importance. So when defining your drivers of satisfaction – what you need from your work – the importance of thoughtfully ranking those needs is implied.

Secondly, since the role work plays in your life comprises abstract intangible needs as well as tangible ones like money, it’s crucial to do all you can to define those abstract needs in terms that are as concrete as possible. What good is thoughtfully prioritizing needs if those needs are poorly defined?

Let’s delve into both of these requirements to help you get to a hierarchy of your drivers of satisfaction that can most productively serve as evaluation criteria for different work options that you may wish to explore.

Identifying and Defining Work-Related Drivers of Satisfaction

When you really take some quality time to think about and write down what’s important to you in your world of work, you’ll inevitably produce a tapestry of positives and negatives – positives you’ll want to accentuate and negatives you’ll want to mitigate or avoid altogether with your choice of work. Springboards for homing in on positive needs include identifying the experiences and circumstances that have made you feel:

·      Happiest

·      Most stimulated

·      Proudest

·      Most fulfilled

·      Most authentic

·      Making the most of your talents/skills

·      Most helpful to others

Springboards for identifying negatives to mitigate or avoid include reflecting on what episodes, circumstances, or even people have ever made you feel:

·      Anxious

·      Diminished

·      Insecure

·      Annoyed

·      Overwhelmed

·      Under-utilized

·      Undervalued

·      Or especially the inverse of your “positives” above (e.g., unhappy, unfulfilled, inauthentic, etc.)

There will typically be somewhere between five and ten criteria that really matter to you when evaluating work options. Any beyond that are likely to be subsets of, or sub-points that further define, those five to ten. Or they will be “noise” – inconsequential in the overall scheme of things, so we want to exclude those for the sake of clarity and focus.

A coaching client of mine who we’ll call Richard, in his early 50’s and ready to make a change, thoughtfully went through the springboards exercise and produced the following criteria (not necessarily in this order; we’ll discuss prioritization shortly) for evaluating work options:

·      Aligns with my values

·      Highly leverages my talent and experience

·      Highly valued by clients/customers

·      Provides financial security

·      Enables healthy work-life balance

·      Gives me more control

·      Reasonable odds for success

·      Allows me to work past retirement age

Richard is now ready to evaluate his options on these criteria, right? Wrong. Not yet. His criteria set is just fine at the high level, but some of these abstractions need much more granular definitions.

I have a three-word mantra that addresses sequence when getting your drivers of satisfaction into sharp focus:Identify > Define > Prioritize. “Identify” and “define” may sound like the same thing. They aren’t. Most work-related needs, other than money and certain benefits, are more abstract than they are concrete. Once an abstract need has been identified, it needs to be defined in a more concrete way to facilitate thoughtful evaluation of alternatives on that need.

For example, “Aligns with my values” might be one of your identified needs as it was for Richard. If so, what are your values? Articulate them. Whether it’s helping people, protecting the environment, taking care of your family, or making lots of money – whatever those things are, be honest. This is not about judging yourself; it’s about zeroing in on what’s authentically important to you. This is not an exercise to be taken lightly. Intangible values are full of loaded words.

As another example, it’s easy to confuse happiness and meaningfulness if you don’t unpack them as best you can to deeply understand what each of those concepts are to you and what expectations you have from them. For some, meaningfulness of work is about improving a particular group of people’s lives. For some it’s the thrill of doing something very well that they thought they might never be able to do. For some it’s about creating a legacy that does some good in the world even after they stop working. For others, it’s work that by its nature has profound moments that aren’t really happy at all, like a hospice worker who eases the passing of the terminally ill, or a grief counselor who helps people go deep into their sorrow and ease their transit to where the light is. You may find, as distinguished psychologist James Hollis suggests, that meaningfulness outweighs happiness – that meaningful moments are, as Hollis puts it, “more moving engagements with others, with mystery, with curiosity and its discoveries, than anything the world names happiness. … Happiness is transient, but meaning abides.”

In whatever way you wrestle with needs like meaningfulness or happiness, you can’t evaluate anything on such criteria without first making these abstractions as specific as possible. What are their component parts? (For you, as each definition is individual.) How do you know them when you see or feel them? What do they do to your senses?

Let’s look at another of Richard’s needs: “More control.” Control over what exactly? Control over how he works? Over when he works? Over who he collaborates with? Over what’s expected of him? You can see the difference between just identifying a need and defining what you’ve identified.

When making career decisions, there’s no getting around a lot of touchy-feely abstractions. But I’ve never seen an abstraction that can’t be at least somewhat concretized. Earlier I mentioned the Strategic Harmony® method for evaluating companies’ alternative investments in innovation, and what we can learn from that approach in personal decision-making. When companies are making products for customers, customer needs – just like your work-related needs – are both tangible and intangible. When, for example, you buy a portable wireless audio speaker to stream music, you likely care about tangibles like price and speaker size. But you may be even more focused on subjective factors: you want that speaker to sound great, be easy to use, and have a cool design. That doesn’t tell engineers and designers what to build unless they know what customers think “great” sound is, what “easy” really means to them, and how they define “cool.”

I reiterate: just because these needs are abstractions doesn’t mean they don’t have discrete component parts. In the context of portable speakers, “great sound” may mean measurable metrics like clarity of vocals and instruments, deep bass, no hum or noise, and can play loud enough without distortion. “Easy” may mean easy to initially set up (simple instructions, all necessary hardware included, easy to connect my smartphone, etc.) and easy to use (intuitive controls, bug-free software, long battery life). I think you’re getting the hang of it. Granted, even for these speakers, some of the more specific attributes are more concrete and more easily measured (like battery life) than others (like intuitive controls). But they are all subsets of the higher-level ‘parent’ attributes (great sound, easy, etc.), helping to define abstractions in a more concrete way. And the more concrete the definition of your work-related needs – your drivers of satisfaction as criteria for evaluating alternatives – the more disciplined and productive your decision-making will be.

The 5-Year-Old Strikes Again

This is where the 5-year-old from Chapter 2 can again be pressed into service. Only this time it’s what instead of why. What really matters. When you identify an abstract need like “work-life balance,” enlist your inner 5-year-old again to put more concrete color on that.

“What does work-life balance mean, Mommy?”

“Well, it means having enough time to do the things I want to do besides my work.”

“What things, Mommy?”

“Things like spending time with you, or going hiking in the woods with you and Daddy, or taking family vacations in faraway places, or making our house pretty, or working in the garden, or even having some of the alone time that all mommies need.”

“Why do you need alone time, Mommy?”

We won’t answer that here (where we have the luxury of ducking the tougher questions like “Why wouldn’t you rather spend that alone time with me, Mommy?”), but you can see that now we’re getting somewhere with making abstractions more concrete and putting a finer point on what’s really important. That inner 5-year-old has just gotten this mommy closer to being able to judge how many working hours a week might be realistic while still allowing time for the “life” part of work-life balance. Then, in turn, it becomes easier for her to evaluate alternative scenarios for work, self-employed or otherwise, on this criterion. (Just to be clear, despite this example, let me assure you that I never want to have to truly separate “life” and “work.” Whether or not you’re your own boss, doing the work that’s right for you will blur that line, as the joys of work and the other parts of your life feed each other.)

Relative Importance of Needs: Prioritization

Now that we’ve identified and defined needs, we can prioritize those drivers of satisfaction with a better sense of what it is we’re prioritizing. (Remember: Identify>Define>Prioritize.) A coaching client we’ll call Angela was a successful sales manager for a well-known technology company. She loved sales, but she felt the pull of being more in control and had been restless for some time – though there was much to like about her company. She was trying to decide between four alternatives: staying with her current employer, taking a sales job at another company, starting an online business with her best friend, or joining a network of sales training professionals that would allow her to work independently as a trainer and be her own boss. She identified seven distinct drivers of satisfaction that collectively defined fulfillment for her. She methodically evaluated her four alternatives on each of those seven criteria. When the criteria were weighted equally, staying with her current employer outscored the other alternatives, appearing to be the best fit. It actually had a moderately strong score on six of her seven criteria. Though it looked like the “winner,” that was before prioritization of criteria was factored in. When she went through a considered process of weighting those criteria in importance, allocating 100 “salience points” across the seven needs, the array looked like this:

Criterion                       Salience (as percent of total criteria)

Need “D”                                            35%

Need “B”                                            20%

Need “G”                                           15%

Need “A”                                           10%

Need “E”                                           10%

Need “C”                                             5%

Need “F”                                             5%

                                                          ____

TOTAL                                               100% of Angela’s

                                                          most significant needs

In other words, even though all seven needs were important to Angela, Need “D” turned out to be seven times more salient than Needs “C” or “F”. (Let’s say “about” seven times, as this type of exercise is at least as qualitative as it is quantitative.) Again, the overarching point here is that all needs are not equal and their differences must be accounted for in decision-making. When the scores for each of her work alternatives were then modified by the relative importance of each criterion, joining the network of sales trainers showed itself as an even better fit than staying in her current job. That’s because, even though sales training had mediocre scores on three of the criteria, it scored well on the three that were most important – high on “B” and very high on “D” and “G”.

I realize this all sounds quite clinical for an exercise as emotional as making career choices. But there is plenty of emotion in identifying and defining what these drivers of satisfaction actually are for you. You’ll want a healthy blend of emotion and rationality in the first two parts of Identify > Define > Prioritize, but prioritization by its nature is best served by translating your subjective instincts and thoughtfulness into some approximation of quantitative outputs. That’s where the salience points come in.

So now that we’ve talked about how to choose among choices, let’s talk about what those choices are. What are your alternative paths? And which one best serves your authentic self?

The many paths to independent work can be overwhelming to sort through. There are more varied opportunities than ever as the incidence of independent work continues to rise, and as more of us have had the experience through the Covid-19 pandemic of working from home with technology-enabled tools. The emerging gig economy creates yet more hybrid possibilities as well. Especially if you’re multi-talented and have lots of interests, the range of options can be as daunting as it is exciting. But even if you’re just choosing between what you’re doing now and one other possibility, a disciplined evaluation on drivers of satisfaction is just as important as when choosing among a basket of multiple alternatives.

Include Your Current Job (if you have one) in Any Evaluation

There’s a reason that “You don’t know what you’ve got till it’s gone” is a cliché. It’s obviously important to know in advance as much as possible about whether that greener grass on the other side is actually greener or less green than the grass you’re in now. I notice that sometimes when clients are comparing alternatives, they forget to include the one they’re living right now as a benchmark. Yet it’s likely the one that you know the most about at this moment.

Sometimes as employees we’ve forgotten how we got to where we are – why we took this job in the first place, and why we were so excited about it (assuming it wasn’t only for the money, which is usually a bad idea). Unless you’re absolutely sure that it’s time to move on, the process of thoughtfully scoring your current job in any evaluation of alternatives can sometimes reconnect you with reasons why you may not really want to leave it. Or it could just confirm that your instincts about it being time for a change are spot on. Either way, there is value in not overlooking the present when deciding about the future.

Inductive Reasoning Pays Off

With your drivers of satisfaction identified, defined, and prioritized, and a clear articulation of alternative paths, you now have the tools you need for making a disciplined choice. At every intersection of each path with each driver – that is, how would each path likely impact each of your needs, positively or negatively – your judgment in scoring those intersections will produce the building blocks for a sounder decision. So by the time you have scored, say, three different paths and your current situation against, say, seven prioritized needs, you’ve produced 28 building blocks weighted by the relative importance of each need. At that point you have inductively built a choice on a foundation of 28 separate and thoughtfully considered decisions, based on the right questions, and preceded by thoughtful ranking of the relative importance of your criteria. You have not only rationalized a choice, but also baked in emotional and psychological considerations.

So, ready to take the plunge? Not so fast. Especially if this will be your first plunge into independent work, a final and crucial safety check is in order. You may have clearly identified what you want and a path to get it, but are you suited to the journey’s demands? That brings us to Lesson 4.

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