Experimental tools for career design

by Evan Ryan

Throughout Fresh Tilled Soil’s Apprentice in User Experience (AUX) program, each apprentice works with a mentor individually, checking in every week to present work for feedback or gain perspective on projects. In this post, Chief Product Strategist, Evan, and his apprentice mentee Trevor share experimental career strategy exercises born from their check-ins that apply the intentionality of product thinking to professional life. Although these thoughts are a work-in-progress, the hope is that the framework and exercises will overturn new thoughts and perspectives on your life, whether you’re a future AUX participant or not.

Each year, two classes of apprentices finish the AUX program and face the same question: “What’s next?” For motivated and skilled designers, there are more paths than ever before, and the economy presents a dizzying diversity of opportunity. Simultaneously, what the labor market values is shifting. As proof of talent, the portfolio reigns supreme. We’ve started to see that what we create and produce is becoming more important than the list of institutions and brands on our resumes.

Our individual values as talent have evolved alongside the market’s values, and our priorities change significantly throughout our careers. Judging opportunities based on stability and salary alone no longer paints a full picture. Increasingly we aim to find opportunities that not only challenge us but that are simultaneously in tune with our deepest interests and core talents.  Because of this, we need new tools to gain a sense of where we are in our professional lives–and where we’re headed. We’re experimenting with these tools from a place of curiosity, and we’re sharing here in order to expand our thinking and hopefully help others navigate these waters.

1. Define your interests

The more interested you are in what you’re doing, the more opportunities will come to you.

List as many interests as you can, without restriction. This is intended to be a brain dump of anything that inspires and/or motivates you, so go wild. Our lists included everything from “product design” to “poetry” to “working with smart people.”

Define your interests

When you’re done with the brain dump, label each interest as either professional, hobby, or educational. These are all important parts of our lives, but for this initial exploration let’s hone in on professional interests. Hobbies and educational pursuits won’t play a big role in this post, but simply acknowledging and labeling them can be very helpful for future reference.

Educational, Hobby, and Professional Interests

As an example, Trevor loves music production–but would never want to be a professional music producer in a studio for eight hours each day, working on other artists’ tracks. He labels Music Production “hobby.” Product design is another interest, and he enjoys the day-in, day-out crunch of solving problems using products, so it’s labeled “professional.” Accounting might one day be professional, but for now Trevor knows next-to-nothing about it and doesn’t have any current intentions of incorporating it into his next professional step, so it’s labeled “educational.” Here, educational refers to something you want to learn for fun. Professional interests can also be related to something you want to learn, but as you’ll see below, we treat educational interests related to professional growth as “desired expertise.” This is an important distinction.

Once you’ve isolated your professional interests, it might be helpful as a final step to break them down even further into the following four categories. This step provides a bit of additional clarity and context around your professional bucket, but is not critical. If you think it might be insightful, try it. If not, move on.

  1. Inspirations and motivations, like “political activism” or “being of service to others”
  2. Active daily interests, like “front-end web development”
  3. Existing expertise, like “journalism”
  4. Desired expertise, like “creative team management”
  5. It’s worth noting that it is possible for an item to be both an “active daily interest” and “existing expertise” at the same time. This is ok.

2. Sight your north star

Recognize that our emotional state is constantly evolving depending on our experience and situation. What we’re interested in will change with time.

From your interests, create your north star. Your north star could be anything–a specific role you want to be in twenty years from now, a general attribute like lifestyle independence, or a focusing lens such as family. It should be a single high level target on the horizon that helps you orient your general direction. You can be elaborate and make it a mission statement, or you can boil it down to a keyword. Having a north star is powerful when making decisions, which we’ll get into more later. As with everything in this framework, your north star can change at any point.

For example, “make things” is a good north star. It’s concise and rather broad, but still defines a core passion that can help set direction. This north star is saying “no matter what the context, I want to be making things.”

3. Chart your river

Using two parallel lines, draw a lane. This is your professional life visualized as a river.

Chart your river

Add perpendicular crossing dotted lines and split up your river into three segments. From top to bottom these represent now, next, and later.

Creating segments in your river

Put your current professional interests in the top “now” section of your river. Put the rest of your professional interests on the shore alongside your river. The interests on the shore are not going away, they’re simply on-deck. You can bring them in or trade them out with others at any point in your journey. For now though you’ve decided you don’t want to pursue them, or won’t be able to just yet.

Charting your segmented river

Draw two more streams for your hobbies and educational interests and fill them in a similar fashion.

At the same time, add your north star at the end of your river.

Fill in your river with your interests

Get creative. Project ahead to the next period representing the next opportunity. What do you want in your lanes? What interests do you want to put back on the shore, or discard entirely?

Attach goal dates to your interests

These rivers represent part of how we spend our lives. We all have limited time before the rivers flow into the sea (if you know what I mean). There’s a lot behind and more ahead, but this exercise helps us focus in on navigating the next few paddles and leaves a lot of flexibility for the currents to change.

4. Map your opportunities

Now it’s time to identify and seek out new opportunities. Thinking of which interests you want in your professional river for the next opportunity, research and list out all possible opportunities you’re interested in. Be specific, but don’t limit yourself only to jobs or new businesses for which you have leads. Spend as much time as you need here. For some people it might take only a few minutes to jot down previously identified opportunities, while others it might take weeks or even months of search and discovery.

Uncovering and creating unique opportunities is an art in itself. There is no right way to do this, and each individual may have a different style. One approach we’d recommend to help you get started is to think big. If you could snap your fingers and work with anyone, who would join. If you could wake up tomorrow and be on a project, what project would that be? As an example, for Trevor this includes everything from going back to school, to working with Bob Moczydlowsky at Techstars Music, to building VR prototypes with Max Weisel at NormalVR.

Once you’ve isolated a set of opportunities that are most interesting to you, compare them against your interests. We recommend a simple table for this. List your primary interests in the Y axis, and your opportunities on the X axis. Go through each opportunity and mark each interest that the opportunity will allow you to pursue. Obviously the more interests that an opportunity matches, the more aligned it is with your core drivers.

Mapping opportunities against interests

Map your opportunities to a risk spectrum and identify your risk tolerance. Everyone has a different threshold for tolerable risk based on a variety of factors like health and lifestyle requirements, dependents, financial obligations, and sense of propriety/decency. For example, right now Trevor’s risk tolerance is very high, given that he has no dependencies nor dependents and is financially and emotionally solvent. However, his risk tolerance will fluctuate as he moves through different phases of his life.

Mapping risk tolerance

In the middle of your risk spectrum, cut a dividing line. Above this line should be opportunities that optimize for output and creation, like new businesses. Below could be opportunities that optimize for input and absorption, like further education or experiential growth.

Evaluating your risk

Evaluate where most of your opportunities fall. What you’re optimizing for (input or output, create or absorb) ties to how much risk you should take.

The overarching philosophy of this exercise is that making decisions based on interests and skill sets is ultimately more fulfilling and effective than making decisions based on salary or prestige, especially as your interests and skills change over time.

When you’re evaluating opportunities and seeking new ones, keep your north star in mind. And remember: all rivers respond to their terrain, whether that’s by wandering through a valley, or cutting a deep canyon through a mountain.

We hope these ideas are helpful in generating new thoughts around choosing opportunities. Please share your perspective with us on Twitter, and we’ll continue to post updates as our model evolves.

About Evan Ryan

Evan is a seasoned product designer and entrepreneur with more than 10 years of experience founding and managing startups in a wide range of verticals....