When Should You Start Looking?

You’re reading an excerpt of Land Your Dream Design Job, a book by Dan Shilov. Filled with hard-won, personal insights, it is a comprehensive guide to landing a product design role in a startup, agency, or tech company, and covers the entire design interview process from beginning to end, for experienced and aspriring designers. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, commentary and future updates, and a high-quality PDF download.

A common question that I sometimes get from folks who are already working is, “What’s a good number of years to stay at a job before you start looking?” Ideally, you’re in a place long enough to make an impact, and you outgrow the position or the company. There’s nothing left to learn, there’s not a clear or appealing path to growth, and you may see a more fruitful opportunity elsewhere. Sometimes this means being at a job for a few months, other times it means working at the same place for a decade.

Of course there are exceptions to this. The company may be doing poorly, is downsizing, or it has a toxic environment that wasn’t apparent during the interviews. This could all happen, and there’s no imperative to stay at a company that doesn’t invest in you. Today’s world offers designers a lot of challenges to address. The trick is to find the right alignment given your strengths and needs.

In her excellent book, Ask Me This Instead, Kendra Haberkorn recommends candidates ask themselves why they would want to run away from a particular job. Sometimes these reasons can be obvious. Other times you might need to do a little soul searching to think about what you value in work and see if these values have changed since you last searched for or accepted a job.

I encourage you to write your reasons out. Similar to the interview retrospective exercise and your reflection at the end of your onboarding—think about the things that are working, what could be improved, and what you’ve learned. In doing so, you may not actually need to look for work, potentially many of these can be fixed on the job through some conversations with your manager. Kendra also suggests asking yourself what job you would run towards. After all, you don’t want to leave a place out of anger just to find yourself in a new role that’s just as bad or worse. Preparation is key—and figuring out what you really want and really value is part of that.

Lastly, you don’t have to be actively looking for opportunities to stay in touch with your network. Develop the relationships before you need them. Talk to recruiters and your peers. Reach out to hiring managers you admire, especially when you’re already in a great role you love. Since you’re already working, there’s no undue pressure to find a job immediately and settle in a less than perfect arrangement just to pay the bills. These conversations will be a lot more enjoyable and will help you get a pulse on the industry and where it’s headed. In the words of Harvey Mackay, “Dig your well before you’re thirsty.”