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This CEO has a tip for planning your career: make decisions as if you're on your deathbed

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Michael Cockburn, founded Desana in 2016.
Michael Cockburn founded Desana in 2016.

  • A CEO shared his tips for making key career decisions: imagine you're on your deathbed. 
  • Michael Cockburn, CEO of Desana, told the BBC that doing so helped him make good choices. 
  • He told Insider the strategy helped him learn what was important and what he'd regret not doing. 

If you're struggling to make a decision about what you want to do with your career, this CEO recommends approaching it from the perspective of your 90-year-old self. 

Michael Cockburn, the CEO of Scottish office-space startup Desana, told the BBC's CEO Secrets series that one thing that helped him earlier in his career was thinking about decisions as if he was on his deathbed at the age of 90. 

Cockburn, 30, started his career as a carpenter, which he enjoyed, but also thought maybe he'd regret doing only that. 

After he finished his apprenticeship, he started his own business aged 19, which he said opened his mind to the idea that he could pursue his own ideas. 

"Running that small consultancy business, working from home, and hating that was the thing that started Desana," he said. 

Cockburn co-founded Desana in Edinburgh in 2016. The app partners with coworking spaces, and enables workers to book a hot desk wherever they need them. In 2021, the company received $4 million in seed funding to grow. 

Cockburn told Insider that while it's easy to get caught up in the potential consequences of your decisions, considering it from the perspective of his future self helped him think more deeply about what was truly important to him. It also gave him more clarity over what he would regret not doing. 

H said: "I'd really regret not doing something although it may be hard and scary. I guess this is something we've all experienced thinking about things we didn't do, and risks we didn't take in the past."

Careers coaches and consultants often recommend approaching decisions from the perspective of your future self as a technique towards achieving your career or life goals

Just as businesses might conduct a detailed "premortem" to weigh up potential costs and benefits, prospective hindsight — as it's sometimes referred — can help people map out the steps they need to follow to achieve their goals.

The author Tim Ferriss practices a technique he refers to as "fear-setting." This is a three-step process in which he maps out goals, potential problems, and solutions in advance.

Cockburn shared some more general advice about approaching decisions. Try to figure out what is important to you, he told Insider. 

"If it's to build something big and interesting, change something you care about, or do something you're passionate about, don't let fear hold you back from doing it," Cockburn added. 

Read the original article on Business Insider
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