The Right Way to Make a Big Career Transition

Embarking on a significant career transition can be daunting, yet exhilarating. It's a journey filled with challenges, learning, and growth. Let's delve into the strategies and insights that can guide you through this transformative phase of your professional life.

Career transitions are like onions. They’re complex and there is usually a lot more to them than we see on the surface.

When Amazon founder Jeff Bezos decided to quit his well-paying hedge fund job, he went to his boss and told him that he was thinking of selling books online

• Selling books online had great potential and e-commerce could be really big
• His boss agreed it was a good idea, but said that it would be a better idea for somebody who didn’t already have a good job
• Bezos came up with the regret minimization framework
• If you’re thinking about quitting your job to make a meaningful career transition, first think about the why, the what, and the when

Expect multiple rejections

Most career transitions and hiring processes rely heavily on past experience

• Most recruiters will nudge you towards a role very similar to your current job, even if you have the skills necessary to transition to a different sector
• Even at Microsoft, it turned out to be much more challenging that I had thought.

Have a backup plan

Create an alternative you can live with when things aren’t going as envisioned or planned

• This can bridge the skill and network gap you might be facing during career transitions
• Today, my backup plan isn’t going back to corporate, but rather Network Capital
• Perhaps it will become a hyper-scalable big tech company, or perhaps it will evolve into a more niche offering.

Set a timeframe

Give yourself one year to make the switch from law to social impact consulting by acquiring the right set of skills, building a tribe of mentors, and networking with industry professionals.

• If it still doesn’t work out, you can rethink your goal or look at accomplishing it in the longer term.

Write your future autobiography

Eventually, how you spend your time is who you become

• This doesn’t have to be 100 pages long, but it does give you an idea of what you want your journey to be
• Conduct a thought experiment and write down what is most important to you

Start by asking yourself why you want to quit your current job.

Is it the culture of the organization, the people you work with, or something else that is bogging you down?

• You might also discover that you love your job, but want to build something new or experiment with a different sector.

Assess yourself

What’s your end goal?

• Write down the steps you will need to take to make your future self proud.
• Understand the challenges that keep you from your goal and the list of things you need to do to get there.

Be realistic

Some transitions are unlikely in the short-term

• Don’t set yourself up for failure by setting unrealistic goals in unrealistic timeframes
• Dream big and act small by trying to take micro-steps in the right direction
• Example: setting up a minimum viable product for Network Capital in the form of a Facebook group

Pro tip: Before leaving your job, try to find ways to experience what your next position might feel like

If you have a passion project, take some time off of work to focus on it

• Use your free time to experiment with the industries or roles you are interested in

Keep the end in mind

Have a mental image of the kind of life you want to build

• Geographically flexibility
• Autonomy over a strict daily schedule
• Create a job that gives your future self a sense of purpose
• A direct connection with the people you are trying to serve

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