We’ve all had those days when the job feels like a paycheck-to-paycheck shuffle in line for whatever the company has to dish out. For me, many were the times when I just felt like escaping for a day, month, or year.
One of the best things about software and IT is that there are so many things to explore and do that there never is a lack of possible directions. With the emergence of cloud, Big Data, machine learning, and even the nascent quantum computing, a curious mind can find lots of great career paths. The question is, which one to choose?
I’ve had several times in my life when things just weren’t working. Usually the cause was staying in one place for too long. For me, unexplored territory is the attraction, and once I’ve learned as much as I want, it’s time to move on.
Regardless, this plan worked for me. Hopefully others can take something away from it and benefit as well.
I am a lot like you; I have been in the same industry for a long time (software) and been through several jobs, some better than most. I am not a job counselor, psychologist or full-time performance or job coach of any kind. Thus, one could argue, I do not have the credentials of a professional—which might mean I am the perfect person to write such a guide. Born of experience, trial by fire and simple to execute, my advice is designed for those that want to get to the heart of the matter quickly. Life truly is short; would you rather wait for great work to come to you (which never seems to happen) or define what it means for you and then create, find or discover it?
Why go through this? There are philosophical ramifications to that question; why even do this? Well, depending on where you are in your life, you might be at the put-in-your-dues stage or perhaps you’re at the chuck-it-all stage. In either case, being comfortable is a big detriment to getting off of your butt or finding out what moves you (at least from a job or career). Only you can find your motivation in that case. Those of us who are (or were) so uncomfortable that something needed to change will put in the (minimal) work to find that dream job and then execute a plan to get there.
Make no mistake: Doing this exercise can be an eye-opening and difficult experience, not due to the complexity of the process, but because you have to honestly face what you truly want to do. It’s very easy to believe that what you’ve been told (or what has been expected of you) is really what resonates with you. One simple way to quickly determine that is to ask yourself, “Would I do it for free?” And with that, we can comfortably move into step one…
Step One: Commit to Be Truthful to Yourself, and See the Process to the End
I know it sounds kind of fuzzy, but in order to get to some kind of outcome, you need to see the process through. It’s hard to see that perhaps what you’ve been doing isn’t moving you any closer towards what you really want to do. This is where being truthful is the hardest part. It’s hard to admit that what you’ve been doing is not your heart’s desire; but more important, it’s hard to be truthful about why you do what you do for work. Is it for fame and fortune? Following the money or following your passion? Working for the “big score” so you can then do what you really want to do? Throughout this process, make sure you truly believe the answers you come up with.
Being truthful requires a personal honesty only found in the privacy of your own mind—the only place where you can be 100 percent honest with yourself. You may not like what you discover there, but without that level of self-honesty, you will never make it through the next steps. I call this step “staring Into the void.”
In many cases, this is as scary and fundamental as questioning your religious beliefs, choice of spouse or political candidate. Staring into the void—even only looking from a career/job perspective—can be intensely scary, mostly because it’s a fundamental examination of who you are. Done correctly, you will come away with either a changed perspective on how you want to contribute your unique skills and talents to the universe (at least), or perhaps an altered world-view (at most). We are shooting for the former scenario; I’ll leave changing your world-view to another writer or religious system.
So how do you “stare?” It varies between people, but personally, honesty has always come by asking myself calibrating questions that I would never repeat to anyone. Things like, “Would I do it for free?” or, “If embarrassment or alienation were not a consideration, would I do it?” Most people can determine if they’re lying to themselves. At least if you’re honest with yourself but never follow your dreams, you can die knowing you made a conscious choice to do that, versus never asking the questions.
Step Two: When Have You Had the Most Fun/Been Fulfilled/Enjoyed the Time You Spent? (Note: Income should not be a factor here.)
This is actually a fun part. For me it was quite easy. Most everyone can remember when they did something that really juiced them up—whether it was work, volunteer work, a hobby, etc. Make a list of each and every one. For those of us who are geeks, put ‘em in a spreadsheet and rank ‘em. Regardless of how you do it, find the things you’ve done that juice you up. To be extra clear: Don’t write down what you think would engage you. We’re looking for real experiences to draw upon.
Be clear by what you think of as “fun.” For example, camping or hiking or summiting a major mountain will include discomfort (muscle pain, long hours of work, high altitude panting, cold nights and pasty cardboard-like food). Post-experience, however, many people find such experiences life-altering or at least fulfilling. I have summited Mt. Whitney twice, both times with new hikers, and nothing could be closer to a life-altering experience as what new hikers who joined us felt. Confusing pure fun (as in “vacation fun”) is a different kind of fun than life-altering, fulfilling kinds of fun. Again, be honest. For most people, fulfilling fun involves contributing your unique values to something else in a personally fulfilling way. Everyone’s definition of this is different. Be honest with what this means for you.
Step Three: Think About (or Write) What You ‘Got’ Out of Those Times
I enjoy skydiving. It is one of those times when the mind becomes free and all focus is narrowed down to the space of about 60 seconds. This begs the question—is skydiving the only thing that makes me feel that way (No), or is it the sense of flying and freedom (Yes)? This step builds on step two and is vital to the task. The reason is that you may enjoy a hobby that can never be a lucrative endeavor—but if you can understand the essence of why that hobby is so engaging to you, you can distill out of it the fulfillment it brings you, and derive that same feeling from another similar (or perhaps dissimilar) activity.
I also like to create and install things. I get a feeling of satisfaction from it, whether I’m setting up a new PC for mom, connecting up high-speed Internet for the first time, or organizing the foundation of a new company. What I get out of each is extremely similar, yet all three vary in how lucrative they are (naturally depending on skill, experience and luck). Find those touch points in this second list you’ve assembled, and use them as your foundation for the next steps.
Abstracting the value (a common theme) versus the activity itself requires some sleuthing and analytical thinking. I recommend asking your friends (without mentioning why you are asking) or colleagues who have joined you in such activities in the past. It may require some precise questioning (which could be irritating) but it’s extremely valuable to you and your journey.
Step Four: From That List of Experiences, Derive a List of Skills That Apply to You
Now that you have a list of things that drive you (there’s no shame in going back and redoing it, even on a regular basis—I tend to get more honest with myself every time I do it and have time to think about the list(s) afterward), you can eke out a list of tentative skills that you possess. Creating? Innovating? Being reliable? Being stable? Working within established guidelines? Again, the more honest you are, the more useful this will prove to you.
I would bet that—assuming you have been true to the process—what you “got” out of those experiences also happened to align with unique skills or strengths that you possess. Few people deeply enjoy activities where they have no skill (i.e. suck at it). If you happen to see this kind of outcome, I would suggest revisiting step one and two and asking yourself: Is this a “big score” theme in your life (which suggests someone else convinced you it was a great thing to do/have/be) or does it truly resonate with you?
Step Five: Go Online and Take a (Free) Personality Test
Many folks (including myself) lack a 100 percent clear perspective on ourselves. That being said, there are numerous (free) sources on the Web that can quantify or bracket the traits we are most likely to bring to a situation, a job or life in general. Some common ones are Myers-Briggs, “Colors,” T-MAP, and so on.
After a series of questions, an analysis is provided by the testing organization quantifying some things you may never have realized about yourself—and yet, on some level, have always known. Within Microsoft, many of us took the Insight Analysis (Colors). The recurring feedback was that relatives and friends must have given feedback to the testers—how else could anyone provide such a level of detail after just a few multiple-choice questions?
Bear in mind, no person or test can provide a complete answer to who you are. What you are looking for is an approximation of the areas in which you are strong (and how you react) as well as where you’re weak. For example, a professional pilot needs a clear head, sharp focus and ability to think their way out of a difficult situation (strengths) but is not often called upon for accounting skills (weaknesses). Though such weaknesses are not totally absent, the idea is that they are not necessarily in the top 10 skills you need to be highly skilled as a pilot.
My own epiphany after such a personality test didn’t happen until later in life. When I did get the feedback (and understood what it meant), I felt like I had just discovered my home planet—and that there were others like me out there, as well. Knowing that first order of approximation as to who I was ended up being a key jumping-off point to what I do today.
Step Six: Go Through Your Personality Test(s) and Note the ‘Ah-Ha’ Experiences as You Review the Jobs/Skills Discovered in Steps Three and Four
Now you can go through your skills list (generated by steps two and three) and reconcile that data with your personality assessment. Why were these lists created in a particular order? You don’t want personality feedback to color or influence the generation of your skills list; the latter should be as unbiased as possible, derived from personal experience.
Step six is where you may have some strong epiphanies (ah-has!) as to why elements on that experiences/skills list proved so memorable and fulfilling. I found that, at those most fulfilling times, I was actually leveraging some (or most) of my personality trait strengths, and depending least on my known weaknesses.
Step Seven: With Your ‘Ah-Ha’ List and Personality Test(s), Go Through Suggested Jobs Found on Sites Detailing Your Personality Type
Now here’s where a more complete picture usually begins to emerge. You may not like what you see (at first), but usually you can grudgingly (or joyfully) admit it just fits, whether it’s a specific job or type of job that emerges. If you’ve been 100 percent honest with yourself, each suggested job stirs some level of excitement or passion within you—passion you might not have felt in a long time. Pick out as many as you can that stir your interest.
Even better: If you tend to be a creative type, there is always the opportunity to create your dream job. A unique alignment of strengths and weaknesses, directed to a purpose with a high need is a fancy way of saying “There’s gold on them thar hills!” Put another way, you may be a born entrepreneur with a sense of what values and services certain people desperately need. If that example doesn’t fit you, no big deal: There are likely hundreds of jobs out there that may closely match your skills and desires. Now you might be better equipped to find them.
Step Eight: Apply Other Factors That Would Influence Your Choice of the List of Jobs
Do you have a large mortgage? A family to feed? Restrictions on traveling? A mortal fear of real estate? Great: Scratch any jobs that would run contrary to those things off your list. If you can’t relocate to accommodate a job change that matches your passion… don’t. Usually there are plenty—or at least a handful—of options that fit your current criteria. Explore the low-hanging fruit before adding more friction to the process. You don’t want to make a job/career/life change tougher than it already is.
Step Nine: Create Your Escape Plan
Not everyone can just up and quit. Planning your escape will be both exciting and motivating. There may be training, certifications, licenses, tools or other things to invest in. The point is—get started! The most liberating feeling is to be on the right path, even if you cannot tread into the promised land tomorrow (or even next month). When you know you’re heading toward the right direction, patience is easier to come by.
While planning your escape is usually right when you’re offered the worst possible thing: A promotion, raise or other similar perk to keep you in your current situation. Avoid such things at all costs!
Stick with the plan—or at least don’t throw it away (short-term gains don’t equal long-term career success and satisfaction). One adage dieters use—“Nothing tastes as good as thin feels”—captures it nicely; similarly, no amount of pay/perk is as enjoyable as a well-chosen career feels at the end of your working days.
Step 10: Wash, Rinse, Repeat
Motivators may change, but purpose seldom (if ever) does. If you have always been excited about building things, it’s virtually guaranteed you will always be excited about building things. Although purpose seldom changes, the execution of that purpose may change often throughout the course of a lifetime. Put simply, if your purpose is to dig holes, one week you may use a shovel (one way to execute), the next a bulldozer, and the third a spoon. All drive to the same purpose, even though they differ in how they approach it. Reviewing your career list is a great way to either remind yourself of how glad you are to do the work that you do, or remind you it’s time to change executions.
So there is the great, secret process to finding your dream job(s). Naturally the only secret not revealed here is to take the first step and be prepared to make mistakes. It is far better to have a flawed plan executed with imperfection than to have a perfect plan go perfectly unexecuted.
JD Marymee is a Technology Evangelist with over 25 years’ experience, including startup launches, as well as an executive for large companies such as Novell and Microsoft. JD is currently a Venture Partner with Pelion Venture Partners, an Architect Evangelist for Microsoft, and co-founder of the technology incubator Technology Innovations Group LLC.
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