Career Exploration Part 1: Build Alternate Realities to Explore

fish bowlsAuthor’s note – As usual, this post started small and has become a multi-post monster. What began as the concept of “alternate realities” that I often use as a frame for discussing how to move forward in a career search blossomed into how to think about exploration more broadly. So we’ll spend a few posts in the coming weeks on some core ideas and a methodology for how to systematically lay out and begin building future opportunities.

Ever wonder how some things just work out professionally for a friend or colleague? Have you thought about why interesting opportunities seem to pop up for them, often times “non-obvious” ones? Are you looking to find more fulfillment but are reluctant to just jump into something you don’t understand?

Well, it’s not “luck”. Some people may be “lucky”, but most successful people I know are only “lucky” if you stay at the surface and ignore their process – however formal or informal. “The more I practice the luckier I get,” is a popular version of this observation. Branch Rickey, a baseball HoF executive who broke the color barrier in MLB when he signed Jackie Robinson, liked to say “Luck is the residue of design”. In other words, you may not be able to make your “luck” but you sure can affect the odds. And over time better odds play out in your favor.

I’m a big believer in developing practices or habits that will lead to both interesting opportunities and making good choices within those opportunities. I have written extensively on a number of practices but the art of building opportunities for yourself systematically over time is subtle and integrates many of the skills and practices I have discussed in the past.

For example, networking is important. But it isn’t an end in itself. Networking for what? One major reason is exploration. I’ll spend the rest of this and my next post laying out how to think about putting in place a thought process and behavioral discipline to begin building the future you seek…even if you don’t know what it is yet.

The steps we’ll discuss include:

1 – Determine motivation: Why am I seeking change?

2 – Define pathways: What are three “alternate realities”?

3 – Get going!: How do I start? (part 2)

4 – Make progress: How many bridges do I need to build or cross? (part 2)

5 – Choose: How do I make quality decisions along the way?

6 – Repeat.

Step 1 – Determine motivation: Why am I seeking change?

It’s important to have a sense of what your underlying motivation is to help think through subsequent steps. In a project management mode, I would urge you to come up with your tightly defined “problem statement”, a one sentence description of what you are trying to accomplish. I don’t mean that here. This process is more impressionistic and evolutionary for most of us.

I’m urging you to get just precise enough to actually start framing options. This means some self-reflection and honesty, maybe some chats with a mentor or peer to test your logic and have it challenged. In other words, you don’t need a well-articulated strategic plan. But you do need to know what matters to you.

Why does this matter at all? Well, how do you brainstorm and prioritize if you don’t know what your goals or current challenges are? For example, imagine the difference between needing change because you want more responsibility doing a thing you like (ambition) versus needing it because you don’t like what you do (nature of work).

Types of needs that I see all the time include: ambition, work environment, nature of work/intellectual stimulation, meaning, balance, geography (ie: I have to move). There are likely others that occur to you. The point is to figure out which one or two are most motivating you. Even if you are miserable and in “anything but this” mode, it’s still worth deconstructing the situation so you don’t just jump from frying pan to fire.

As I’ve mentioned before, one of my favorite quotes is the Cheshire Cat telling Alice, “if you don’t know where you are going, any road will take you there.” Prior post on “figuring out what you want”.

2 – Define pathways: What are three “alternate realities”?

There are a number of factors at play (doing great work networking etc.), but one strategy I see successful people apply effectively is what I term “exploring alternate realities”. Think of these as distinct paths forward. They represent conscious efforts to be active beyond the day-to-day of your current role. Think “mini-experiments”. I try not to get too specific or deterministic about this. They just need to make sense in your own mind.

Let me explain my thinking.

There is a strong incentive in many of our careers to keep our heads down and get stuff done. So much work to get done and so little time. Then there’s the rest of your life. The part that includes your family, friends, interests, health…much of what we say matters. All of that conspires to rob you of time for longer term thinking. Much of it really is urgent and/or important and demands your attention. I WANT to see my kids soccer game and I NEED to respond to my boss when appropriate. But if you let all of the day to day consume you, in the end you’ll keep on the path or in the rut you are in now.

How do I claw back time to invest in my long term ideas?

To get some measure of control I urge you to do the time equivalent of “paying yourself first”, a concept taught in retirement savings. Block a set period of time during the week or commit to a set amount of activity. We’ll talk below about what to do with the time, but if you don’t make the time you can’t get anything done.

I get frustrated when people (myself included) whine about not “having” time. If it’s important you’ll MAKE the time. If you can’t make the time, then it’s apparently not that important to you. It may be one hour per week doing research, maybe it’s having coffee with one person a week, whatever…. Pick something reasonable and achievable and build from there.

What do I explore?

In step 1, we thought about motivations asking ourselves “why change”.

Based on the answer to that, start jotting down some ideas about what might be better given where you are now.  Frame broadly at first and don’t be too judgmental. When starting you don’t know what you don’t know. You don’t even need to be too specific. What gets you excited? What do you keep coming back to? Where do you find meaning? There are many useful thought exercises to run through. But do it. And write down your thinking.

(Note: I didn’t ask “am I happy?” Happiness gets overrated and a great deal of research is emerging that tells us “happiness” is a byproduct of finding meaning. It’s not an end in itself. If you feel like something is missing, focus on answering “what?”. This should lead you to a number of ideas for what might be more fulfilling.)

Turn this thinking into what I call “potential alternate realities”. Imagining yourself in another place, situation, company, role…whatever it may be helps to frame potential pathways to explore. Framing a limited number of reasonably distinct themes helps organize your time and thinking.

I think three is the right number. More than that and you haven’t focused, less and you’re not really laying out enough options. Conceptually, it’s often helpful to think about the three as “succeeding on my current path” as well as exploring a “lateral” and a “divergent” opportunity. My distinctions are a bit arbitrary, but let me explain them.

Current path: Even if you hate where you are, you need to consider plugging in and exploring the opportunities right in front of you. First, you don’t want to have to leave. Be a strong contributor, build meaningful connections and show interest in progression. In this context, you want to understand what is required for progression, what people get paid, how responsibilities and work may change. Knowing this (and much more) will strongly inform your thinking about career. How can you make plans if you don’t know and how can you hope to progress if you’re not demonstrating an interest in progressing?

Example: Perhaps the work gets more interesting if you gain a promotion and gain leadership responsibility.

Lateral path: Is it what you do or just where you’re doing it? One promising path is often thinking about one step moves away from where you are. Think “I like finance, just not retail” or “I like retail, but not finance”. In either case, you have a natural entree’ into a discussion about potential moves and it’s more a matter of networking to explore.

Example: You love your company, but not your role. Maybe there’s a better fit in another group.

Divergent path: Do you have a dream that is totally different than where you are? What is it and why? It’s important to articulate these as they may take more time and effort to explore or build bridges to.

This can be the most challenging as it is often your “dream job”. You may be very emotionally invested in it and have all sorts of positive feelings about the idea. I see 3 kinds of challenges here that we’ll take on a bit in step 3 and beyond.

Challenge 1: It’s my dream, so I’m afraid to engage it because I like the dream.

Challenge 2: It’s my dream, so I want to jump into it without looking.

Challenge 3: It’s so far from what I do now that I don’t try because it seems an immense challenge (intellectually, time, financially etc.)  and I have a day job.

Example: You’re an accountant, but want to be an author. Really any major change.

Note: A word about “themes”. Focusing too narrowly on a role or a specific opportunity can be unhelpful. I was at a talk recently by Chip Heath and he refers to it as “narrow framing” in his new book Decisive. I tell people to “squint” at ideas to not focus too tightly too early on small details. See if the broad contours of an area are interesting before you go too deep. For example, saying “I am interested in marketing” may be more helpful than “I want to be a Brand Manager at company X”. Brand management is quite a specific role and frames out lots of potentially interesting (and more plentiful) marketing opportunities.

That’s it for now.  Next time we’ll delve into how to explore…


1. Make time.

2. Answer “what’s my motivation?”

3. Define 3 “alternate realities” you’d like to explore.

This series continues here:

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