In a recent LinkedIn post, Jason Feifer discusses the outdated nature of traditional five-year career plans, drawing on insights from former LinkedIn CEO Ryan Roslansky. Feifer argues that in today’s rapidly changing technological landscape, rigid long-term plans can become a hindrance rather than a guide.
Feifer highlights Roslansky’s perspective that focusing on short-term learning and experience acquisition is a more effective approach. As Roslansky suggests:
“I would much recommend people focus on maybe the next few months and a couple of things that aren’t a plan, but [rather] what do you want to learn?” Ryan says. “What type of experiences do you want to get? That’s, I think, the right mental model in this environment.”
The Pitfalls of Long-Term Planning
Feifer aligns with this view, sharing his personal career philosophy that eschews lengthy, predetermined plans. He explains that his approach has always been to view jobs as educational opportunities rather than destinations. This perspective shifts the focus from tenure to tangible skill development and personal growth.
A Focus on Learning and Growth
According to Feifer, the key question he has consistently asked himself throughout his career is, “What did I come here to learn? And have I learned it?” This self-assessment tool dictates his career trajectory. If the answer is yes, it signals that it’s time to seek new learning experiences elsewhere.
Feifer illustrates this with a personal anecdote:
I took a job at Men’s Health. Not because I cared about Men’s Health (I didn’t), but because it taught me a certain kind of editing. Then every other job was taken for a new skillset — either in editing or management.
This strategy underscores his belief that jobs should be stepping stones for acquiring specific skills and knowledge, rather than long-term commitments.
Optimizing for Agility in a Changing World
The core of Feifer’s argument, echoing Roslansky’s sentiment, is the necessity of agility. He contends that while having a plan is not inherently bad, the true wisdom lies in being prepared to abandon it as circumstances evolve. This adaptability is crucial for maintaining relevance and value in the professional sphere.
Feifer summarizes this philosophy with a powerful takeaway:
Having a plan is fine. But plan to abandon the plan. Optimize for growth. Because the more agile you are today, the more valuable you’ll be tomorrow.
By emphasizing continuous learning and a willingness to pivot, Feifer suggests that professionals can better navigate the uncertainties of technological advancement and career progression. This proactive and adaptive mindset, he implies, is the modern antidote to the rigid, often ineffective, five-year career plan.
📝 About This Content
This article is based on insights shared by Jason Feifer on LinkedIn.
📅 Originally posted on April 27, 2026 | View original post on LinkedIn →