How to handle getting stuck
- The ideal job search, and why it rarely happens that way
- Questions for self-reflection
- When you consider shifting your focus
- Be organized, and diagnose where in the funnel you’re having issues
- Make sure you’ve done enough informational interviews that you aren’t learning from them anymore
- Consider getting outside help
- Make sure to max out your interview skills before investing in expensive credentials
- Switching focus doesn’t have to mean changing your goal
The ideal job search, and why it rarely happens that way
This book has laid out a logical progression for how to go about a job search. In an ideal world, you’d march from chapter to chapter in order, building skills as you need them, until you arrive at this point in the book knowing everything you need to know. You’d then go out, get more first-round interviews than you know what to do with, and get offers from some of those jobs.
However, this will almost never happen. Job searching is messy. You might get stuck on learning cold email or informational interviewing for a long time, or learn from informational interviews that the job you thought you wanted doesn’t sound that great after all, or get an offer for something you’re not that excited about before you know if you got your dream job or not.
The goal of this chapter is to give you some strategies and ideas to work with when the job search doesn’t go as planned, and you’re thinking about changing what kinds of jobs you’re looking for.
Questions for self-reflection
Whether things are going very well or not so well, it’s helpful to reflect on your job search to notice any big problems or changes early. I recommend you put aside at least an hour every two weeks to think about some of these questions:
- How do I feel about my job search right now? Does it seem like my current approach is going well?
- What are the 1 or 2 careers that I’m currently going for? Am I effectively spending most of my time focused on those goals?
Note: don’t just answer a job title like “Product Manager” here. A better answer would at least include geography, company size, and some idea of industry, like “Product Manager at a 100–500 person software company up to an hour’s commute from my home.” - What traits about myself am I currently presenting to interviewers as my biggest strengths? Are those traits resonating with the interviewers? If not, should I be changing the way I present the trait, or should I pick another of my strengths?
- What target qualities do I think these jobs want in an ideal candidate? Have I validated that they want these things through informational interviews and kept my target quality tracker for this job up to date?
- What do I think these jobs have that I want? Have I validated through informational interviews that these sorts of roles satisfy what I need in a job?
- Have I made progress in my job search compared to two weeks ago? If not, what should I consider doing differently?
See next section for some ideas.
Stepping back and thinking about your search from this perspective should help you see if you need to make some changes. If you are dissatisfied with the career you’re shooting for or with your lack of progress, the next section has some ideas about what to do.
When you consider shifting your focus
I’ll define a switch in focus as when you change what title, geography, company size, or industry you want to focus on. Most people switch either because another job fits their preferences better, or because they think getting what they really want is too hard or impossible.
The simpler reason: another job fits what you want better
There are a lot of reasons your preferences can change. Especially when people are thinking about switching careers, it’s very common that once they start interviewing they find out that there are some big negatives about their target role, or they find some huge positives about an adjacent role. For example, I have a client that thought he wanted to be in marketing but after interviewing found business development, a career he’d never heard of before, to be a much better fit for his background and goals. Life circumstances can also force a change, if you have a need to move geographies or need to prioritize health benefits more highly in your next job.
When another job fits what you want better, it’s usually a good idea to pursue that instead of what you were looking at before. However, I’d caution against changing your target lightly. Every time you switch your target job, you need to do many informational interviews to develop expertise on the topic, redo your target qualities for the role, learn how to deal with new types of interview questions, and more. If you switch every few weeks, you may never get good enough at that role’s interview style to get a job.
It’s OK to explore a lot of different possible roles early in a job search, especially if you don’t know what you want. But if you find yourself changing targets every few months or more after you get started, consider staying focused on one role for a while even if something else feels more exciting.
The more complex reason: getting what you want seems too hard
Knowing when to switch your focus because the job search is hard is a very difficult question, since there are no clear rules about whether you should keep going or try something else. Some transitions, like trying to move from one year’s experience as a customer support rep with no management, design, or programming experience into a product management role, are unlikely to work. In these cases, it’s relatively simple to say that switching focus is a good idea, but in most cases it’s much less clear.
Below are a few things to consider if you’re having a hard time with the current mix of job title / company size / geography / industry that you’re shooting for.
Be organized, and diagnose where in the funnel you’re having issues
If you haven’t been keeping a job search master tracker up to date, now would be a great time to start. Knowing that you’re not getting the job you want isn’t specific enough to improve. Instead, if you look at the funnel in the Unusually Difficult system, you should be able to diagnose where in the process you’re struggling, in order to know where to try and improve. Once you know if you’re struggling to:
- Find interesting companies in the first place
- Find possibly interesting people at those companies
- Get those people to talk with you
- Turn those conversations into strong recommendations
- Turn strong recommendations into first-round interviews
- Etc.
Then you’ll be able to attack that specific problem. For most of the process of getting a first-round interview, your job searching skills will matter more than your qualifications, so hard work should be able to get you to the interview.
Make sure you’ve done enough informational interviews that you aren’t learning from them anymore
In my own job searches, I’ve had companies where I’ve interviewed more than five people before applying. This doesn’t make sense to do for every single company you come across, but if you really want to work somewhere or aren’t having as much success as you want, try doing many learning interviews before applying. Each interview gives you deeper material to ask about in the next one, and you should find yourself impressing people with your knowledge by the time you’re done.
Two rules of thumb about informational interviewing that might help are:
- If you’re still learning a lot every interview, you’ll probably become a stronger applicant by doing another one
- You should be able to learn enough about a company from doing ten informational interviews that you come to truly believe (not just state convincingly for interview purposes) that you would be the very best person to hire for the role, because you know what is important better than anyone else.
If you never come to believe that you’re the best for the role, then you might need to be more confident, you might need to work on your informational interviewing skills, or you might genuinely not be qualified for the role.
Consider getting outside help
I find it a bit strange that it’s commonplace to hire plumbers, wedding planners, painters, and other specialized professionals to help out with parts of our lives, but hiring a job search coach is not something most people do.
Most people spend a huge fraction of their week working. Additionally, having enough salary to pay the bills, or an extra two weeks of vacation, or more interesting coworkers for eight hours a day, or an hour less spent commuting in traffic hundreds of times per year will probably have a much bigger effect on their happiness than a dripping sink, mediocre wedding cake, or badly painted wall.
If you think I could be helpful to you as a 1:1 coach, please get in touch at coaching@matthewfdupont.com. I’ll be happy to see if working with each other could be a fit, and if not I’ll do my best to recommend you to someone who’s a better fit.
I don’t have a comprehensive list of coaches all over the world (a few are in the resources section), but would be happy to help you try and figure out who might be good to work with so that I can add them to the list.
Make sure to max out your interview skills before investing in expensive credentials
It’s always possible to be more qualified. You could go back to school and get a higher degree, go to one of the many bootcamps available for most tech careers, or get a certification from an online course. These options usually feel safe: few people will criticize what you’re doing, and they give you the comfort of structure in the messy and unclear world of job searching.
I’m not saying these options are wrong, but I do think many people reach for these without putting in the more challenging work on their job searching and interview skills. It’s a lot cheaper in terms of money and time to do the embarrassing work of recording practice interviews and working on your responses for two weeks than to go get a Master’s degree. If your interviews aren’t successful, take a hard and honest look at your interview skills before deciding you need more qualification.
Switching focus doesn’t have to mean changing your goal
In the opening of this chapter, I talked about how an inexperienced customer support rep can’t easily switch right into product management. However, two of the best PMs I’ve had the pleasure of working with were once in that exact position: in customer support with no other work experience.
They didn’t immediately quit and try to become PMs, though. They looked at what the requirements to become a PM were, became great at their current jobs, were promoted to leading the support team, used that leadership to strongly influence product decisions and build their reputation, and then were able to switch into PM based on that track record.
If you decide you can’t move directly to the job you eventually want, use informational interviews and LinkedIn to try and find people with similar backgrounds to where you are now, and see what steps they took to eventually arrive at the job you want. Your next move can still be a move towards your goal, even if it takes a few years to get there.