Career Exploration Part 2: Test Alternate Realities & Build Bridges to Your Future

fish bowlsIn my last post I laid out a process first few steps to take in finding new opportunities. In this post I’ll offer some advice on how to get going on the ideas you generated.

First a reminder of the process:

  1. Determine motivation: Why am I seeking change? (Part 1)
  2. Define pathways: What are three “alternate realities”? (Part 1)
  3. Get going!: How do I start?
  4. Make progress: How many bridges do I need to build or cross?
  5. Choose: How do I make quality decisions along the way?
  6. Repeat.

Step 3 – Get going!: How do I start?

How do I explore?

Having just defined several interesting “alternate realities”, it’s time to get going. But how?

I’m a big believer in a personal version of “evolution” (which is underpinned by natural selection). Evolution stacks up small changes that over time can lead to a big change. In other words, iterating, testing in a (somewhat) systematic way. This lets us discard bad ideas quickly with minimal cost and build on good ones.

I am distinctly NOT a believer in the opposite approach. Call it the “trust the fall” approach. In this version of change, we jump off the cliff into the water we can’t see the bottom of. Hopefully the water is deep, cool and refreshing. But there’s a strong possibility that it’s in fact bitter cold, shallow and has rocks right below the surface.

So the path forward is about creating opportunities to discover, learn and test opportunities.

First, Explore – Understand and set context.

When you don’t know what you don’t know, it’s important to figure it out. So how do I explore?

Obviously, you want to do secondary research. The web offers a treasure trove of content that I not going to discuss. I assume intelligent people can do some research and think a little laterally about new areas.

So what does primary research look like? It consists largely of talking to other humans. Whether you call it networking, informational interviewing, exploring…whatever; at some point you need to get off the dime and start talking to people.

For a “current path” exploration, it’s about getting on the radar of relevant folks at work. Think 360′ view and reputation building. So make sure you’ve talked with folks about what makes a person “promotable”, discussed career paths, compensation, culture etc. You want to understand both what it takes to succeed and whether it’s a place you want to succeed. Also, the act of asking affects how people see you. Just make sure you’re over-delivering in your day to day work.

For a “lateral path”, it’s often straight networking. If you like your function, but not your company then join a trade group or find folks with similar roles at other organizations. Go find people to explore different organizations to understand them and get on people’s radar.

For a “divergent path”, you’ll need to think about several stages because this is a more complicated process. The explore stage is also very network and relationship driven.

Then, Test – Build small experiments to determine both interest and aptitude.

In innovation and design, we teach low impact/high learning pilots or trials. This is the same idea. What are “simulations” you can run?

For smaller moves it might be doing a project in another group at work. Don’t turn this into a physics problem. The idea is to get quick and dirty feedback.

For bigger changes you’ll need to be a bit more creative. Think you want to teach? Guest lecture in a class. Owning a bakery sound great? Try getting into a farmers market or lower threshold commitment to see if you like it. A friend of mine took a woodworking class and realized he HATED it. Good to know before you buy expensive equipment and quit your day job…

Finally, Build – Escalate tests into marketable, committed engagement.

Turn teaching into leading a single class. An acquaintance escalated their interest in coaching into a part time commitment working evenings 2-4 hours per week. Take on a project with a target organization as “church work”. There are many, many ways to do this. You are limited only by your creativity and drive.

The point is to “bridge” yourself into new areas while also making sure to “try before you buy”. It’s a two way street. You are testing interest and aptitude while building a book of work that is potentially marketable.

I sometimes think of this process as building a mosaic…lots of little steps can build a larger picture over time.

Step 4 – Make progress: How many bridges do I need to build or cross?

Progress comes in several forms.

Eliminating Things

For me, it took a PhD program and three years to realize I didn’t want to be a history professor. For some people it takes one day doing something new to realize it’s a poor fit. Some paths are actually exciting, but you just can’t make the math work financially.

These are great things to learn before making hard to reverse commitments. So embrace and celebrate eliminating paths were experiments have “failed”. Consider it pruning the rose bush to ensure the vitality of the plant.

Bridge Building

Another form of progress is what I describe as “bridge building”. It’s important to develop a perspective on how many steps away from your goal you are. In other words how many gaps do you need to “bridge”? If you identify gaps, a major part of moving forward needs to be filling enough of them that you’ll both be seen as credible by others and be confident enough in yourself to keep going.

I recently interviewed someone for a position in my organization. They were coming from a very different industry, but had invested 2-3 years in bridging. Starting with mentoring, moving into a formal (very) part time role and were perfectly credible as a full time candidate. I and others believed their career positioning because their interest was clearly authentic and they could offer tangible examples of how they could be successful.

Making progress for the “current” and “lateral” paths can be as simple as quietly applying for new positions at your current or other potential employers. It’s in many ways easier to visualize and quantify the progress. Did I apply for jobs? How many? Did I network? Enough? etc.

Divergent Path Progress

“Divergent” progress can be tougher to measure because you often don’t know what you don’t know. You’ll have to treat these paths as a bit more of an experimental design. I teach a concept called “discovery driven planning” popularized by Rita Gunther McGrath. The basic premise is when you don’t know much about a new industry or business; treat it like a research project. Identify major assumptions that must be true for success. For example, “I have to be able earn xxx” or “I need …”

Then focus your time and energy on the most important unknowns. You’ll also be able to measure progress against at least a few defined milestones.

One interesting aside. The more assertive and capable you are at this process, the greater the odds of you “creating” an opportunity that may not have existed before. We all know people who’ve “worked themselves into a job” or had something created for them.

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

I don’t have more useful advice here beyond get to be honest with yourself and don’t fail to actually make decisions.

When I say be honest with yourself I mean to really assess progress and fit. Are you moving forward? Can you muster energy for what it takes to move in a new direction? Do you like where you’re going? Are you (objectively) good at it?

Deciding along the way is important too. My friend Jon taught me early in my career about “the fallacy of infinite possibilities”. Many of us can try to defer deciding to keep options open. But this becomes a decision of sorts, just a passive one. Paths close as you fail to act on them. So be sure to kill bad ideas and embrace and pursue ones you are excited about.

Step 6 – Repeat.

This is a never ending loop. You’ll just run it at different speeds at different times in your career.


1 – Test or “try before you buy”

2 – Persistence matters

3 – Don’t be afraid to decide

Next time, I’ll walk through a particular experience of my own as an example of how I implement these ideas in my own life.

In case you missed it, here is Part 1.

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