Resolving Your Uncertainties

Gaining clarity

Now that you’ve started to compare and assess your options, how do you take action and move forward?

In the last chapter, we talked about creating a methodology to help structure your decision-making process. As you looked at your options and started making some comparisons, you likely came up against some things that you’re unsure about.

Maybe, for instance, you imagine that a career path could be impactful but don’t know how many people you could actually help or if this work would make a significant difference in the world. Or you like the idea of a job but you aren’t sure if the day-to-day tasks would actually stimulate enough to sustain motivation. Or you think you’d be really great in a different career path that you haven’t tried, but you don’t have enough similar work experience to feel confident in switching fields. Without having clarity on these uncertainties, it’s hard to make an informed decision about your next best step.

There’s no way to answer every question or resolve every uncertainty before taking a next step or deciding on a career path to pursue. Oftentimes, this can feel paralyzing, leading people to never make a change in their trajectory or take any action at all. To avoid getting stuck in a state of speculation, it helps to prioritize your questions depending on how important they are to actually taking a next step. For example, are there some questions that would be nice to learn more about but that wouldn’t change your mind about what to do next? Are there others that seem especially pressing, as though you can’t move forward without knowing the answer? Once we have some idea of which uncertainties to focus on, we can start to find the quickest means we have to tackle them. 

In this chapter, we’ll discuss how to identify, prioritize, and resolve some of the major uncertainties you have about taking your next career step. By the end of it, you should have an idea of what types of questions you might want to focus on and what kinds of actions would help to clarify your decision. 

If you’re not at the point of making a decision and are only thinking about shifting your career trajectory sometime in the future, that’s fine too. Try envisioning what it would be like to apply this process to a future decision. It may give you some insight to what sorts of questions might come up and how you can tackle uncertainties sooner than later. To illustrate what this could look like, let’s return to Lucía’s search for an impactful and meaningful career.

Lucía decides that journalism and advanced studies in philosophy could be the two most promising of her options. Both paths rate highly on her three important factors, and she feels excited about them. Yet at this point, she’s unsure which direction to go. As she looks over her methodology table, she starts to take note of the uncertainties that came up when she was making her ratings.

  • If I pursued a PhD in Philosophy, what would I do from there? How could this path lead to helping others? What would the day-to-day work look like?
  • Do many journalists get to choose the topics they write about? How impactful could this path be in the long run?
  • Would I genuinely dislike the writing tasks involved with policy careers or am I just assuming this?
  • Do I prefer in-depth, research-based writing enough to not pursue a career in nonprofit communications?

Then she comes up with a few extra questions that didn’t come up in the table but that seem potentially important to making her decision.

  • Is it financially feasible to return to school for Philosophy? Would I be able to secure a fellowship and make enough to get by?
  • Would I have to move cities for either of these paths?
  • Would I have to return to school to pursue a career in journalism? How difficult is it to get into the field? 

Because there’s a lot Lucía doesn’t know about each option, she tries to narrow and prioritize whatever information would help her take some next steps. It seems like the most important things to figure out are the practical ways to help others with a philosophy education, the funding options available for pursuing an advanced degree, and the extent of freedom/flexibility she’d have in journalism roles to write about important issues.

To start tackling these uncertainties, she first does a bit of online research to check how financially feasible it would be to pursue an advanced degree in Philosophy. Most of the programs she’s interested in offer sufficient funding packages. She also finds an external fellowship to apply for that could help with extra costs. 

Next, she wants to figure out how (and if) she could use her philosophy education to get a job that helps others. There are a lot of examples of exceptional people doing great things with their philosophy background, but it isn’t very clear how they got there. She decides to commit to a few days of research to find some people in the field to ask about job options for applying philosophy. Lucía also plans to find a few established journalists to talk with. Hopefully, this will give her a better idea of how impactful journalism could be as a career and how much flexibility she could have to write about important problems. She also looks into different fellowships that would allow her to explore journalism without fully committing to it as a career path.

If it turns out that she could make a meaningful impact on the world with a career in Philosophy and afford the extra education, Lucía is confident in focusing on this option over journalism. However, if a career in journalism could help people and philosophy doesn’t seem to provide many practical job opportunities, she would prioritize jobs in journalism.

As Lucía’s case illustrates, breaking down this process can make tackling your uncertainties a bit more manageable. We think it’s helpful to look at your questions through three stages: identify, prioritize: resolve.

The process


You don’t have to figure out every unknown before taking action. Start by identifying some of the questions that come up as you look over your methodology table. Think about areas where you were very unsure about rating. Were there certain factors you had no idea how to rate? Is there something you assume but don’t know for sure?

Then, ask yourself if there’s other important questions that don’t come up in the table but that you’d need to gain clarity on. These can be anything from detailed questions about the kind of work you’d be doing to broad questions about the importance of the problem you’d work on. At this point, try quickly jotting down all the major uncertainties that come to mind.


Now that you have a list of questions, you can start to prioritize the most important ones. These tend to be make-or-break questions that could alter how you think about your options or potentially change what action you decide to take. To get a sense of which questions you need to answer before moving forward, try asking yourself:

  • Is there specific information I could learn that would change my intuition or assumption about an option?
  • What new insight would make me change my top option?
  • What is something that could change my mind about whether or not to pursue one option over another?
  • Which questions will prevent me from making a decision or taking a next step?.

Keep in mind, your career is more of a journey than a final destination. Prioritizing your most important questions doesn’t mean forgetting about the more minor or less pressing uncertainties. Whatever opportunity you pursue next, you’ll continue learning more about the industry, role, and yourself—resolving questions along the way. Right now, we’re focused on figuring out which questions are important enough to figure out before moving forward.


Now that you have an idea of which questions to prioritize, it’s time to make an actionable plan for resolving them. 

There are all sorts of ways you can go about gaining insight about your options and lessening uncertainty about important questions. To break down the process and save yourself time, it can help to use a tiered approach.

For example, start with the lowest time commitment action (like a bit of online research). After doing this, gauge how much clarity or information it provides. If it’s enough to take a next step or help make your decision, then you can cross this question off. But if you’re still pretty unsure and feel unsatisfied, move on to an action that takes a bit more time (like completing a small project or work-test). For every major question you have around your career decision, keep starting with small actions and moving up until you feel confident enough to go forward.

Examples of actions to take

A few hours:

  • Internet research
  • Talk to people you know that could provide some insight
  • Visit open days for relevant degrees, companies, etc.
  • Reach out to one-on-one career consulting

A few days:

  • Find an expert or professional to talk with (through mutual acquaintances, or by reaching out with a short and thoughtful email)
  • Do a small project or mini course on the subject

Weeks to months:

  • Complete an online course
  • Volunteer for an organization or company doing similar work
  • Look for fellowships, internships, and short-term experiences in the field
  • Try a longer term project (e.g. helping with a research project, starting a blog to practice long-form writing, building online tools or a website)


  • Pursuing a versatile degree
  • Trying a job out for a time

Resolving your uncertainties could take a few hours or a few months, and you’ll often need to make a decision before gaining all the clarity you’d like. What’s important is gaining enough information that you can take a next step, then continuing to update your plan as you gain experience and insights.

Next up, we’ll put everything together to take some concrete next steps.