Five Steps to Clarity When You Need to Make an Important Career or Life Decision

Have you ever needed to make a major career or life decision and just can’t seem to commit? 

You could be choosing between two competing job offers or trying to decide if you should pivot to a new career direction. Or you could just be trying to decide if you should paint your bedroom gray.

As a coach, I find that many people come to me when they’re facing exactly these kinds of choices (well — maybe not the paint-the-bedroom-gray thing) and just can’t seem to get to a firm decision. They’re anxious and often describe themselves as “confused” or “a little lost.” 

After spending time with them, it usually becomes clear that the information they need to commit to a decision or direction is already there, floating around in their heads. 

And that’s the problem. It’s floating around in their heads.

From moment to moment, certain thoughts and feelings drift to the front of their mind and capture their full attention, only to be pushed aside by other thoughts and feelings. At any given moment, they’re focusing on only one thought or feeling and aren’t able to see the connections and patterns. The roadmap that points to the right decision is fuzzy. 

So they feel lost. And without help, they risk making a decision about job choice, for example, based on whatever has floated to the front of their mind at that moment. That could be excitement about a breakthrough level of compensation, the attraction of a lofty title, or the charismatic personality of a potential boss.

My role as a coach is to help people who are facing these types of decisions collect their thoughts and feelings — all of them — and then name them, clarify them, and identify the connections and patterns among them. 

But not everyone has a coach at the ready every time they’re faced with a major decision. So here are 5 steps you can take to do some of this work without professional help.

The Process

Step 1: Talk

For most of the people I work with, the simple act of talking and having someone listen attentively is clarifying, and even therapeutic. It’s helpful for them to express the thoughts and feelings that have been floating around in their heads and say them out loud. This process works best, of course, when you have someone listening attentively who can then ask follow-up questions.

A little background.

For several years, in addition to coaching, I worked as a certified moderator and interviewer on marketing research projects. The bulk of my work was helping consumers and customers express their thoughts and feelings out loud and then clarify them. At the end of an interview, the person sitting across from me often commented that the interview had felt “a little like therapy” and that they hadn’t fully realized that they felt a certain way about a product, service or experience in their life. I find the same kind of thing happens in coaching sessions. The simple act of talking and responding to questions helps people come to realize that they feel a certain way about a role, an industry, a company, or a city. 

As a member of the coaching staff at the Harvard Business School, I’ve had the good fortune to be trained by Dr. Timothy Butler. He teaches that people typically have an implicit knowledge of what’s true and meaningful for them. It’s only by expressing this ‘felt sense’ in actual language that they achieve the clarity they need to take action. This immediately made sense to me given my experience in marketing research. If you’re interested in Tim’s work, check out his two books, Getting Unstuck and The Four Elements. 

You don’t necessarily need to work with a coach like me to have productive conversations that will help clarify your thoughts about a big decision you need to make related to your career or life. 

But you do need to talk with someone.

The person you choose doesn’t need to know you or your work very well, or even your job function or industry. They just need to be a good listener who helps you get thoughts and feelings out of your head and is curious enough about them to ask a few follow-up questions.

When you choose a person to speak with, some of the questions you should be asking yourself are:

1. How comfortable do I feel with this person? Can I be honest with them without jeopardizing relationships, my current situation, or future opportunities?
2. Does this person have an agenda, even if that agenda is just being supportive?
3. Is this person a good listener? Or do I think this person would be a good listener?
4. Does this person tend to give advice first rather than asking questions? 
5. Can this person resist making the focus of the conversation about themself?

Once you've identified the right person or person, schedule some time to talk. Let them know that you'd like to share the details of a decision you need to make and that you'd like to talk it through with them. And that you'd appreciate it if they could help you sort through it, ask questions, and even challenge you.

Don't set it up as an advice-seeking session or it will put pressure on them to do just that: give advice. It may be helpful to get their advice, but only after you've had an opportunity to get the thoughts that have been floating around your head out into the open and examined. Encourage them in a conversational way to ask questions and challenge you. Things like:

"Is there anything I've shared that's not entirely clear to you?"

"Do you think I'm being consistent in how I'm approaching this?"

"Do you think I'm contradicting myself?"

Come up with a few questions of your own that will encourage your conversation partner to be on the lookout for consistencies and inconsistencies in what you're sharing.

Writing your thoughts and feelings down is the most important step in the process of achieving greater clarity when it comes to decision-making.

Step 2: Write

During your conversation, or immediately after, take notes. Writing your thoughts and feelings down is the most important step in the process of achieving greater clarity when it comes to decision-making. And you don’t want to be trying to remember everything you said much later that day — or worse — later that week. You’ll likely forget many of the things you said and end up focusing on just one or two of them, which is counterproductive. You’re trying to develop a broader view of the factors that might influence your decision and not focus on just one or two things. 

The roadmap to the right decision is likely going to be complex. If you have two competing job offers, you don’t want to be making the decision about which one you’re going to take based on compensation alone, for example. The nature of the role, the culture and reputation of the company, the profile of your boss, and a myriad of other considerations will likely come into play. You want to capture and crystallize your thoughts about as many of those things as possible.

Your notes don’t have to be full sentences either. As a moderator and interviewer, I needed to take notes while doing a number of different things simultaneously: maintaining a connection with the person I was interviewing, following the flow, questions, and timings laid out in a discussion guide, keeping track of follow-up questions I wanted to ask, and responding to the occasional prompt from a client hidden behind a one-way mirror. Two things I found helpful to do when I wanted to remain engaged in the conversation and not get lost in my note-taking:

1. In the left margin of whatever you’re writing on, keep track of the main topic of the conversation, such as “role” or “company.” As the topic changes or returns to a previous one, keep track of what you’re talking about. It will help you in the next step. 
2. As you’re talking, write down words and phrases that strike you as particularly important or meaningful. They’ll either come to you easily, without hesitation or they’ll require some effort and it will be hard to find exactly the right words. Don’t aim for perfection in your notes, just get the words and phrases written down.

Step 3: Clarify

Not too long after your conversation ends, return to your notes. Do the following:

1. For words and phrases that feel important to you and the meaning is clear, circle them.
2. For words and phrases that are unclear or seem ambiguous, draw a squiggly line under them.
3. For the words and phrases that have the squiggly line under them, draw an arrow out from them and write new words that help bring the thought or feeling into focus. Repeat this step if necessary. A good question to ask yourself is “Would someone else understand exactly what this means?” If not, keep refining.

Step 4: Identify Patterns

Once you’re done identifying the most important words and phrases and clarifying the ones that might be unclear or ambiguous, do the following:

1. Read back through your notes and look for consistent ideas or themes among the circled words and phrases.
2. Look also for ideas that seem to be inconsistent or in opposition to one another. 
3. Mark these consistencies and inconsistencies in whatever way makes sense to you. I use a checkmark to note positive themes (something the person I’m coaching wants) and an ‘X’ to note negative themes (something they don’t want). I typically draw plain lines to connect thematically consistent words and phrases and double-headed arrows to connect thematically inconsistent or oppositional words and phrases.

If you're adept at your note-taking and your conversation partner is reasonably skilled at challenging you based on the follow-up questions I suggested above, some of the clarification in Step 3 and pattern recognition in Step 4 may already be reflected in your notes by the end of your conversation. If not, do this work as soon after the conversation as is practical.

Step 4: Generalize and Prioritize

Once you’ve identified your consistent themes and those that are in opposition to one another:

1. Write a few or more sentences that summarize what you’ve learned.
2. If appropriate, assign a priority level to the sentences or ideas you’ve identified relative to the decision you currently need to make.

For an example of what your notes might look like as a result of this process, see below.

Step 5: Take Action

At this point, the important factors leading to your ultimate decision should be more apparent. The roadmap should be clearer 

If it’s not, and it may not be, try repeating the cycle. Talk to more people, take notes, analyze, and further clarify your thoughts and feelings. While your decision may still not be an easy one to make, you’ll at least be making it with greater self-knowledge and confidence. A portion of that confidence will come from knowing that you’ve dug deep and have considered the decision from multiple angles.

An Example

Imagine that in one of your conversations, you’re talking about two companies — Company A and Company B —  that have made you competing offers. In the process of sharing your thoughts about Company A, you say that it would be an “exciting place to work.” When you’re talking about Company B, you say that it’s “a good opportunity.” So how do you choose between an exciting place to work and a good opportunity?

You dig a little deeper and follow the directions in Steps 2 and 3 outlined above. “Exciting place to work” and “good opportunity” might mean different things to different people. You draw squiggly lines underneath them. Upon some reflection and refinement, you determine that Company A would be an "exciting place to work" because you consider them to be "innovative" and that you'd have the opportunity to work on "frequent new product launches." And the good opportunity at Company B seems attractive at first because they’re a "market leader" and have a "stable product line." But having a stable product line means that there likely wouldn’t be many opportunities to launch new products. Maybe you’re at a place in your career where getting to launch new products would be truly interesting and would also provide marketable skills. 

While “exciting place to work” and “good opportunity” both seem positive at the outset, it turns out that they’re actually in opposition to one another once you’ve dug a little deeper. While this analysis might not result in a final decision about whether to accept the offer from Company A or Company B, it seems like Company A has a compelling advantage. 

You then capture that insight in a fully-formed sentence: I'd rather have the experience of working on new products than the opportunity to be associated with a market-leading brand.

Conclusion

When you’re feeling confused or stuck and you just can’t make an important decision about your career or life, having a few conversations can help bring things into focus and provide the clarity you need to move forward. 

Find a person to talk to who’s a good listener and likely to be curious and ask follow-up questions. Keep track of the thoughts that emerge from your conversation by taking notes. Try some of the note-taking techniques I've described above that I learned when I was a market researcher. You’ll be able to capture thoughts and ideas and then analyze them fairly quickly. Write what you think you’ve learned. If one conversation doesn’t provide enough clarity to make your decision with a sufficient degree of confidence, then try having more.

This goes for all kinds of career and life decisions, from which industry you should be working in to whether or not you should paint your bedroom gray. Try it.

If you have a major career decision on the horizon and sense that it’s going to be a difficult one, consider some coaching time. I’d be happy to help you consider your options from all the angles.