Lessons from a Job Search

Dan Saffer
4 min readMay 19, 2021


Note: I didn’t really want to write this article, but am doing so at others’ urging hoping it’ll give other job hunters some hope, some insights, or at least a laugh.

There’s an idea held by many that the more experienced you are, the more accomplished you are, the better your network, the easier it is to find a job. I’m here to debunk this. I have 20+ years of experience, 10+ years in design management, a master’s degree in design from a great school, a seemingly good reputation, and my last role was at a high-profile company. Still, I was ghosted, given take-home design exercises, was told job offers were coming that never materialized, given “personality quizzes” that I apparently didn’t pass, and suffered the same sorts of indignities during my exhaustive search for a new role.

For about eight months, I hunted for a job. Unlike the last time I was out of work, I had no trouble landing interviews. Some weeks, I was doing interviews every day, multiple times a day, for several different companies. Three months into my search, I even stopped applying for jobs because I was sure one of the five companies I was in final talks with would come through. Spoiler: none of them did, and I looked for another five months. Lesson #1: Always Be Applying.

I applied for a Design Director job where they asked me what programming languages I could code in. I said in the (unskippable) form field: You don’t want me doing any production code. I never heard from them.

By my estimation, I applied for over 60 jobs. I heard back from about 40 of those. I made it to the “present your portfolio” stage with over 20 of them. I finally got job offers from two places. While it shouldn’t be, the job market is a numbers game.

Email: “We have decided to consider other applicants who are more closely aligned with the basic qualifications required for this role.” Basic qualifications? That’s cold. (Needless to say, my qualifications far exceeded what was in the job listing.)

My network wasn’t much help. Sure, some people fed me leads (thank you), but when it came to actually landing jobs, I didn’t get any offers from companies where my friends and colleagues were at the company. Yep, even when they were the hiring manager for the role I was applying for. Lesson #2: Your network will only get you so far.

I was told by a startup in the middle of the second interview that they’d want me in the office three days a week. Reminder: this was during Covid.

Lesson #3: Ageism in tech is real. I really didn’t want to believe this, but it’s hard to not think that had I been 10 years or more younger, I would have easily landed some of these jobs. I’d get to the very last round and some mysterious qualification would appear or I’d just get a No. Sometimes this was after the first time they would see me on video. Some experience: great. A lot of experience: not great. And this was after I had, several years before, done all the tricks we people over 40 do, like lopping off 10 years of work and college graduation dates from our resumes and LinkedIn.

Me: Do you have any reservations about hiring me for this role?
Them: No! You seem like a great fit.
[One week later]
Them: After much consideration…

Considering the people I was talking to were mostly designers, I found Lesson #4 hard to comprehend but here it is: Unless the work in your portfolio is closely related to the work their company does, they will have trouble extrapolating it to their domain. You need to do this work (if you can) for them. Draw paralells (e.g. “This complexity I dealt with in this project is probably similar to the kind of complexity I would deal with at your company.”). The role you’re most likely to get is the role they can easily see you in. Make it easy for them. Connect the dots. When I didn’t do this, I didn’t get the job. Even for jobs I was deeply qualified for.

Job Listing: 4+ years of managerial experience
My Experience: 10 years as a manager
Recruiter: “We ultimately decided to go with others who had more extensive managerial experience.”

Lesson #5: Don’t expect much feedback. I was fortunate that some people I interviewed with gave me some feedback about why I didn’t get the job. Those people: classy. But I interviewed for jobs where I had extensive conversations and portfolio reviews going up to founders/C-level executives and got back a form letter. Not classy. Or, even better, was ghosted.

Lesson #6: This shit takes time. My last two job searches have each taken over six months to do. And this is during the time when design jobs are booming. Expect your job search to take 150% more time than you think it will.

Some portfolio tips I learned the hard way

▪️ Cut to the chase. Your intro of yourself should take no more than five minutes.
▪️ Animations and movies > static images. Everyone likes moving things. Makes your presentation more interesting to see things in action.
▪️ Show a summary slide for each project. How long it took, what was your role, what was the goal.
▪️ What were the problems you were trying to solve and the context for the project. Tell a story, help the audience understand. What didn’t you know when you started the project.
▪️ Show results. How did your work move the needle?

Good luck out there, job seekers. My next post will be more cheerful, when I talk about the role I got and why I’m excited about it.