I’m wondering how you might go about defining a career path in a diagonal direction. I have identified a senior managing role I would love, that I think I would excel at, in an industry I have zero experience in (journalism). I have a sense of how I can progress in my current field (UX research) and how I might break into an entry- or mid-level position in another field, but the idea of working toward a senior position in a new field leaves me with a head full of question marks.

How can I (and my manager) build a roadmap in this direction?

Emma: Long-shot jobs are definitely intimidating. It’s way easier — still hard, but way easier — to gear up for jobs when you’re a shoo-in. I’ve always felt a little cringe of shame when I set my sights on a long shot. Is someone going to laugh at my overconfidence? Hire me only to realize I’m a phony?

Andy: I’ve definitely been there. You’ve probably heard that men are likely to apply when they meet 60% of the qualifications, but women don’t until they hit all 100%. Tara Sophia Mohr asked why and most of the reasons for women were some variety of “believing that the job qualifications are real requirements, and seeing the hiring process as more by-the-book and true to the on-paper guidelines than it really is.” It’s not that they weren’t confident they could do the job — like you, they thought they would excel at it. They simply believed the required qualifications were actually required.

Emma: People get jobs they aren’t “qualified” for all the time. One of my best bosses came from outside my industry, and I’ve watched folks from various backgrounds join the ranks at every level at every job I’ve ever worked. You’ll probably never be a Perfect Fit and thankfully, you don’t need to be.

Andy: It’s probably not surprising that we think you should go for it, right now, no “working toward” the role required. If you have the time and energy: just apply!

Emma: Yes! There’s something about this senior management job that sparkles for you, and that’s not an everyday thing. If nothing else, applying forces you to figure out what that sparkle is all about, and then helps propel you down the path toward it.

Andy: So, let’s talk about applying. All you need to do is: find the job’s big takeaways, write a compelling cover letter, tailor your resume, and send it off.

Emma: Don’t get me wrong: I love the idea of strategizing ways to accentuate your qualifications for a stretch role — and super love that your manager is down to help. We’ll get to that in a second, but I also want to flag that it’s possible to spend a lot of time and resources bolstering unnecessarily.

Andy: It’s the tar pit for a lot of perfectionists: their cringe avoidance is so strong that they stay trapped in never-ending bolstering.

Emma: No previous role is the exact analogue of your next one. Your job as an applicant is to explicitly connect the two: You want this and this, and here is proof that I fulfill those things. 

Andy: The this and this of the job are your big takeaways. Focus your sights on writing your application to those things.

Where to Find the This and This of a Job Posting

1. The application questions

Most jobs list loads of qualities and responsibilities and experiences that are “required,” but the most effective applications zero in the biggest takeaways. To find what’s really important, look to the application questions, not just the posting.

Let’s look at this Managing Director role at The Pudding as an example. The job description is over 1,000 words long and covers everything from ideal personality traits to worldview to operational excellence to creative leadership. But when you click through to the application, it’s suddenly quite apparent what the big takeaways are: creative process chops and developing/mentoring others. Those are the only two things you need to apply convincingly.

Such a clear-eyed job description can be really intimidating. It fuels all those feelings of, “They know exactly what they want and that’s not me.” Just remember, they haven’t met you yet. When they were drafting this JD, they didn’t even know they could hire someone like you. You’ll connect those dots for them in your cover letter and resume.

2. Your own best skills

Lots of jobs are so broad and wide-reaching in their requirements that there’s nothing to home in on. Instead of trying to cover everything, see this as a You Pick Two creation: grilled cheese + cup of tomato soup, or Caesar salad + chicken panini, etc.

This Managing Editor role at Gossip Cop and Oola is much broader than the role at The Pudding. That means you get to pick your big takeaways. You could go with your analytical mindset and the way you’ve used performance metrics to build successful programs. Or, you could talk about your effective freelance interactions and workflow improvements. If you have done lifestyle content before, you could use those results as one of your big takeaways.

When the job post defines the hierarchy or explicitly indicates the big takeaways, believe it! Use those. When a job post is more open ended, choose your own two big takeaways.

Emma: Once you have your two big takeaways, step two is demonstrating the proof. You’ll probably need to be a little bit creative. The type of 1:1 examples you might include in an application for a shoo-in role don’t exist when it’s a long-shot. Your mission is to make your application make sense.

One strategy is to simply explain how your unrelated experience is ta da! actually related. I may have never managed the production process on a creative team, but I have been a dog walker for a long time, and here is a very clear, cogent, and convincing explanation as to why that applies. I’m not going to lie: this is pretty tough to do the longer the shot is.

Andy: Which, cue the 🎶 ad break music 🎶

Our course makes the whole process of applying to jobs (both shoo-in and long-shot) so much easier. We walk you step by step through putting together your resume and cover letter, with worksheets and prompts and videos and fill-in-the-blank templates. You can sign up to have us give feedback on your application materials, or even have us on your team for your entire job search. Use code SUPERDEAL to get 60% off.

🎶 Now back to our regular programming 🎶

Emma: If you have more time — say, you have an eye on a long-shot role at a company you admire, and want to feel ready to go for it in the next 18 months — big takeaways are your blueprint. They show you exactly where you can bulk up your experience and exposure to super-charge your belief that you are right for the role, and super-charge how convincing your application is.

Andy: Bring those takeaways to your next 1-on-1 and share them with your boss. Even better, come with a few ideas for how you can build them in your current job: take on a special project, contribute to the blog, volunteer for a committee.

Emma: Be the point person for an upcoming initiative, take on a mentee, improve the training program, research a broken process on your team and improve it. Ask for funds to enroll in training or a certificate program.

Andy: Of course, you can do all this outside of your 9-5, and in some cases you’ll probably have to. But the great thing about building up your experience within your current job is that they’re already already paying you to be there. Let them pay for your dream career, too!

Emma: Good luck. Please keep us posted.