How to investigate your career uncertainties and make a judgement call

Find the full career planning series here.
The most important sections in each article are marked with ★’s.

★Step back, reflect, and make your final list of key uncertainties

Career planning involves so much uncertainty that it’s easy to feel paralysed. To tackle your uncertainty, approach your investigation like a scientist. Make hypotheses, investigate them empirically, and update.

You’ve listed key uncertainties throughout the articles in this series. Now we’re going to gather them all up, check whether you’ve missed any, prioritise which to investigate, and work out what investigation to do.

Gather up uncertainties

You have accumulated key uncertainties through this process, including about:

• Which global problems are most pressing (and your values and worldview)
• Your best potential longer-term paths
• What your best next career steps should be
• What your backup options should be

Copy and paste them into Section 7.1.1 of your template.

Now here are some ways to reflect on your whole plan, check you haven’t missed any key uncertainties, and start resolving some of them.

Get some overall feedback

Often what the people we advise find most helpful at this point is to show their plan to others — other people can help spot assumptions you’re making that may seem obvious to you but really aren’t.

One exercise is to make a copy of your template and send it to a couple of friends or advisors for comments. If it’s long and messy with notes, you can just send your plan A, next step ideas, and uncertainties.

This not only helps to identify further key uncertainties, but can probably help you start answering some uncertainties too.

Try to get feedback from people who understand your aim to have an impact and who can be supportive while they challenge your thinking. A ‘career-planning partner’ can be great if you can find someone to trade career plans with — you can critique each other’s plans and help each other generate more options, plus provide moral support. Our advisors may be able to help too.

How do you reach out to people? It depends on your relationship — but if the person is someone you don’t know as well or with whom you have a more formal relationship, these tips may be helpful. In these cases, it’s better to send one or two specific questions rather than your whole plan.

It can often be easier to reach out to people if you’re both part of a community focused on making a positive difference, because then they know helping you will help them further your shared goals.

If you get some negative feedback, don’t respond hastily. If your plan is unconventional — which is likely, if you’re targeting something neglected — probably not everyone is going to agree with it. Try to understand the reasons behind their negative reaction, and decide whether to adjust. If the reasons are unclear, perhaps wait to see if others have a similar reaction or if it’s an isolated example.

You can adjust your list of uncertainties in Section 7.1.1 of your template in light of what you learn.

Ask yourself how you feel about your plan

Now that you’ve done a lot of explicit thinking, it’s a good time to listen to your gut.

Bring the different aspects of your plan to mind. Is there something you feel uneasy about, or that feels aversive? Does something feel ‘off’? It’s okay if this is vague.

How do you feel about your plan in general? Anxious / excited / sad / frustrated / calm / guilty etc.?

While we don’t agree with the mantra that people should ‘go with their gut’, especially when it comes to working out something as complex and abstract as how to have an impact, we also don’t think you should ignore it altogether.

Your intuition is good at evaluating things like what you’re excited by and which people are good to work with, which are important inputs into the decision.

An uneasy gut reaction may also be a sign you’ve uncovered a problem with the plan that hasn’t yet made it to your conscious mind. Emotions contain signals about what to pay attention to, although they don’t always accurately represent reality.

If you have a negative emotion or gut reaction, try to understand what it’s about.

Then, consider whether you should change your plan or investigate further. You might find your intuition has picked up a mistake that you can fix. The ideal is for your analysis, emotions, and intuitions to all line up.

Alternatively, you might realise it’s best to push ahead anyway — it’s normal to be, say, worried about the future, even if you’ve done all the steps worth taking to mitigate the risks. And sometimes your gut can get stuck on something that it shouldn’t — as we know from the study of neuroses and biases.

If you’ve investigated what your gut feeling is about and you don’t endorse the concern, acknowledge the feeling and try to let it go.

If you think the concern is a good one, see if you can mitigate it by adjusting your plan.

If you can’t identify what’s behind the feeling, it might be best to push ahead in the meantime and keep checking in on it until it becomes clear what it’s about.

Again, adjust your list of uncertainties in Section 7.1.1 of your template in light of what you learned.

★Prioritise your key uncertainties

Now you can make an overall ranking of your key uncertainties, including both those you identified throughout this process and any you just uncovered. Base your ranking on:

• How easy the uncertainties seem to be to resolve
• How much difference resolving them would make to your career plan

Write them down in rank order in Section 7.2 of your template. Feel free to leave off any that seem like they definitely won’t be worth investigating.

★Make a plan to investigate

Now that you know what your top uncertainties are, you have a choice:

1. Investigate to reduce some of your top uncertainties, and then revise your plan in light of what you learn.
2. Attempt to put your plan into action now (bearing in mind you can update it later).

In reality, these two options overlap. Often one of the most useful things you can do is to just apply to lots of jobs and talk to lots of people, which both helps to put your plan into action and gives you valuable information about opportunities and your fit for them. We often see people agonise over a choice between different paths, when if they’d made lots of applications, the best path would have become obvious.

However, it’s still useful to roughly divide into ‘investigation mode’ and ‘action mode’. Focus more on action if your key uncertainties are relatively minor or will be hard to make progress on. Likewise, sometimes your key uncertainties are best resolved just by trying to put your plan into action and seeing how it turns out — you can always revise your plan in 6–24 months depending on what happens.

Otherwise, since your career involves so much time, it’s most likely worth some further investigation.

How to investigate your key uncertainties

• The most useful step is often to talk to people. The right person can give you more up-to-date and personalised information than what you’ll be able to find in a book or online. People we advise are often surprised at how willing people are to help. See some email scripts for informational interviews and asking for advice. (Bear in mind that when you’re talking to these people, they are probably also informally interviewing you — see our advice on preparing for interviews in a separate article.)
• Do ‘desk’ research, such as searching Google. As part of this, you can see everything we’ve written by topic to see if we’ve covered it before.
• Look for ways to test your uncertainties. For instance, simply applying to lots of jobs is often one of the best ways to learn about your fit (and can double as pursuing your next steps).

Make sure to start with the lowest-cost ways to gain information.

We like to think in terms of a ‘ladder’ of tests, from least to most costly. For example, one such ladder might look like this:

• First read our relevant career reviews and do some Google searches to learn the basics (1–2h).
• Then speak to someone in the area (2h).
• Then speak to three more people who work in the area and read one or two books (20h). You could also consider speaking to a career advisor who specialises in this area.
• Then look for a project that might take 1–4 weeks of work, like applying to jobs, volunteering in a related role, or starting a blog on the policy area you want to focus on. If you’ve done the previous step, you’ll know what’s best.
• Only then consider taking on a 2–24 month commitment, like a work placement, internship, or graduate study. At this point, being offered a trial position with an organisation for a couple of months can also be an advantage, because it means both parties will make an effort to quickly assess your fit.

Make a list of ways you’ll investigate your highest priority uncertainties in Section 7.3 of your template.

If needed, adjust your plan

After you’ve done some investigation, you might want to update your plan.

In reality, this is not a single step — you might go through several loops of investigation and updating.

You might also start to put your plan into action, and then later realise you need to revise it.

We cover taking action in the next article for simplicity, but in reality you might jump back and forth between acting and adjusting your plan several times.

We mention investigating your uncertainties again in the next article as a type of ‘next action’, so you can move on to that part before finishing the investigations you want to do, and you’ll be prompted again to dive into them.

★Make a judgement call

Eventually, you will need to make a judgement call about the key elements of your plan. This can be difficult. As we noted, it may not be possible to feel confident in your answers. So the aim isn’t to feel confident. Rather, it’s to make a reasonable decision given the information and time available.

If you’ve already completed the steps we cover throughout this career planning series, you’ve already put most of the best decision-making advice into practice. You have:

• Broadened your options
• Clarified your strategic priorities
• Tried to narrow down systematically, such as by scoring them on your criteria
• Sought feedback from others
• Asked why you might be wrong
• Investigated your key uncertainties
• Considered backup options

Eventually, you just have to make a decision. If you’ve done just half of what we’ve covered, you’ve done a lot, and are likely making a much better decision than you would have otherwise.

So make a judgement call for now. In Section 7.4 of your template, write out your best guess for your career plan, including:

• A list of problems you might help solve
• Your strategic priorities
• A Plan A, consisting in a best-guess next step and some top longer-term options it might help you work toward
• Your options for a Plan B, i.e. promising alternatives to your Plan A
• A Plan Z

If you’re still hesitating, we have one final step that should help give you a bit of peace of mind: setting review points. Remember that your career is a series of experiments, and you don’t have to figure it all out right away.

★Set review points

It’s easy to constantly second-guess your plan, but that’s probably not the best way to live. You should spend most of your time focused on succeeding within, learning from, and enjoying whatever you’re currently doing.

At the same time, it’s easy to just continue with what you happen to be currently doing for too long.

A way to avoid both issues is to set an explicit review point — a trigger to reassess your plan:

• One option is to pick a timeframe, typically 6–24 months (shorter when you’re more uncertain and learning a lot; longer when you’re more settled). Around the new year is often a nice time, and we have an annual career review tool for this purpose.
• Another option is to consider when you’ll next gain significant information about your career, and reassess then. For instance, if you’re transitioning careers, decide to review if a year passes and you haven’t yet found a new role. Or if you’re on the tenure clock as an academic, you could decide to review halfway through.

Whatever point you choose, it can be useful to set a concrete intention to review at that point in Section 7.5 of your template — and to set yourself some kind of reminder, for example in your calendar.

What to do when you hit your review point

• If you’ve had a significant positive update in favour of the path you’re currently on, then probably stick with it; if you’ve had a significant negative update, seriously consider switching.
• If you’ve learned about any new options that might be significantly better than your current focus, consider switching — otherwise continue.

We lead you through some more questions to reflect on in our annual career review tool.

If you do decide to change your plan, you can restart this planning process. Don’t worry, it’ll be a lot quicker the next time around, since you’ll be able to only focus on what’s changed since last time.