Evaluating career paths & jobs: A guide to understanding what you want


What are the most important things you're looking for in a job at this point in your life? How do you assess the pros and cons of various opportunities to ensure you're making the right tradeoffs? Are there ways to make the whole process less overwhelming to ensure you're focused on the most productive activities and prioritizing the right initiatives?

When it comes to finding a job, a lot of attention is often focused on what employers are looking for and how to present yourself in a way that makes you the best candidate. But what’s equally important and maybe even more difficult is defining and understanding what you’re looking for, what you really want. More specifically, what are the factors that matter to you—compensation, commute, title, organization culture, boss chemistry, the product or service, employer brand recognition, amount of travel, flexibility, training, critical mass of peers, and more. Many of the same factors apply to all of us, but their relative importance inevitably varies from person to person and might even vary for yourself over time. Your 20-something self, fresh out of school, might prioritize being in a cool office downtown with people your age and opportunities to get on the road. However, your 30-something self might be a new mom who wants a role that allows working from home and little to no travel.

The reality is that you won’t be able to get everything you want—which is true of jobs as well as spouses, houses, cars, friends, and pretty much everything in life—so understanding the trade-offs you’re willing to make can help ensure you end up in a position that will best fit your unique needs at a given point in your career and life more broadly. Meanwhile, being realistic about what you’re going to get—in terms of compensation, title, and more—can help you prevent analysis-paralysis and/or waiting for the amazing thing to emerge that simply doesn’t exist. One might call this challenge the “romanticism prison,” and it can effectively limit you and immobilize your decision-making by creating expectations from people, places, and things that are simply unattainable and unrealistic, ultimately creating a cycle of self-defeat.


Setting high goals and expectations for yourself is definitely a great thing, but it’s important to do it in a way that recognizes tradeoffs are unavoidable. Figuring out how to evaluate them effectively can make or break your success and happiness. To help establish a framework that enables you to assess different career paths, opportunities, and offers, we’ve created the Ask HeR Job Navigator, featuring a set of tools designed to help you define what matters, evaluate the key factors that characterize each job opportunity, and make the right tradeoffs.

First, complete the Decision Matrix to plot various career paths or roles you’re pursuing to determine what falls in the magical intersection of ambitious and achievable. There might be a myriad of adjacent roles that cross multiple industries or perhaps multiple roles within a given sector that might be considered as part of this process.

Second, build out a plan for each of those paths or targeted roles with the 10 Steps to Ambitious Achievement worksheet, detailing the steps you’re going to take and when you’re going to take them to end up in the right place.


As you start to execute your plan and positions emerge that you need to evaluate in more detail, map them into the Job Scorecard  to harness what might be a confusing set of pros and cons into a quantitative framework that can help the right path for you become clearer. (Before you start filling out the Job Scorecard, just make sure you save a new copy first! To save it, tap “File” and then select “Make a copy”). If you'd like to see an example of a Job Scorecard that's been filled out already, check it out here. 

One last thing to consider before you embark on the tactical part of your heroine’s journey is what point you are in your drama/comedy/action sequence. Consider your decisions carefully in the context of this chapter in your life, gaining perspective on what’s best for you at this time while also considering how it fits into the broader narrative, or how it will set you up for success over the longer haul. In the world of making trade-offs, that might mean taking something that feels like a lateral move or accepting a pay cut in order to gain a great opportunity with an organization that you really want to be a part of over the longer haul. The point is that most career journeys aren’t linear and predictable, but are instead a meandering collection of events that might not seem related at a micro level but together add up to something pretty unexpected, awesome, and especially “you” over the longer haul.

At any and every point in your process, we recommend checking out Women@Work’s Mentor Marketplace. These experienced women are available to workshop your resume, dry run an interview, explore one career path vs. another, or even complete the scorecard to help you evaluate two or more opportunities you might have. Just explore the “Supply” of mentors to find those who look most relevant to the field and role you want to pursue and “buy” Office Hours (for free, of course!) with one or more of these amazing women who are willing and able to help.

About Alexis


Alexis Harding is Women@Work’s resident HR expert. A long-time HR professional based in the Boston area, Alexis has rich experience in the HR departments of several large institutions over nearly two decades. She is here to engage with your questions about a range of topics that might be impacting your career and your overall success.


About Christina


Christina Van Houten is the founder of Women@Work. Based in Boston, she is a senior executive at one of the world’s largest enterprise technology companies. Christina has worked since she could as a teenager and has relished the experiences and empowerment a long-time career has provided her. She’s eager to support women of all ages, career stages, professions, geos, and backgrounds to help them find their way to the best possible life they can achieve.

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