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Where your work meets your life. See more from Ascend here.

When Amazon founder Jeff Bezos was deciding when to quit his well-paying hedge fund job, he went to his boss and told him that he was thinking of selling books online. He had already been talking to him about the power of the internet, but for the first time, he was seriously considering quitting to become an entrepreneur. His boss was startled to hear that someone would actually leave a coveted investing job to work on something with so many unknowns. After all, aren't good investors experts in evaluating risk?

His boss decided to take him out for a two-hour walk in Central Park in New York City. He wanted to understand what was going on in Bezos' mind. During the walk, Bezos managed to convince him that 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 was given 48 hours to make a final decision.

To figure out the next steps in his career, Bezos came up with the regret minimization framework, a simple mental model to minimize the number of regrets in the long run. He asked himself what he would regret more when he was 80 years old: Trying to build something he had strong conviction in and failing, or failing to give it a try? He realized that not trying would haunt him every day.

When he thought about his career transition, keeping the regret minimization framework in mind, quitting turned out to be an incredibly easy decision. He left the hedge fund in the middle of the year and walked away from his massive annual bonus.

Whether or not you are pursuing a passion or side hustle, confused about quitting your job for a new one, or just looking for a change, know that it's not a straightforward decision. It requires careful planning and thinking. I can say that with some conviction because I've had to make this tricky decision myself. Last year, in the middle of the pandemic, I quit my job at Microsoft to work full-time on my passion project. I loved my work, but the more I reflected on my core values, the kind of life I wanted to build, and the way I wanted to use my skills, the more it became clear to me that entrepreneurship was the way forward.

I had nurtured my passion project as a side hustle for four years: Network Capital, a global peer-to-peer networking community of 100,000+ ambitious and curious millennials. There were so many questions running through my head during this time. Why should I quit to make this my full-time job? Is this what I really want? When should I quit? Poet Mary Oliver's words kept ringing in my head: "What is it you plan to do with your one wild and precious life?"

Most importantly, I wondered if I would regret not giving it a shot. But making that decision turned out to be more complex that I had thought.

Transitions aren't just about doing something different. A career transition is a lifestyle redesign that often entails rethinking how you want to feel at the end of the day, how you want to spend your time, and how this relates to your longer term goals. When you feel this need for change, it isn't necessarily related to a fancier title or more money, but your inner voice whispering that you could do more, be more, experience and achieve more.

If you're thinking about quitting your job to make a meaningful career transition, first think about the why, the what, and the when.

WHY (do you want to change)

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

Is it the culture of the organization, is it the people you work with, or is there something else bogging you down? Like me, you might also discover that you love your job, but you want to build something new or experiment with a different sector. It is critical to be radically honest with yourself and think things through.

I decided to conduct an experiment to figure out my career transition. For the past four years, I worked on building Network Capital on nights and over weekends. I took two weeks off from work to focus solely on this task. That is when I realized that I could make so much more progress on my side-hustle with focused effort.

That focused effort not only energized me, but also propelled a whole bunch of new product roadmaps. In fact, I came up with the idea of launching cohort-based-fellowships during that time. That was my "why" and it made me realize that I enjoyed dedicating most of my waking hours to my side-hustle, even though I loved my day job.

Pro tip:

Before leaving your job, try to find ways to experience what your next position might feel like. Does it feel better than what you are doing now? Is it worth committing to this change? If you are able, take some time off of work — even just a week — to focus on your passion project. If you don't have a passion project and are just looking for something new, use your free time (weekends or after hours) to experiment with the industries or roles you are interested in. This might mean volunteering, job shadowing, or even conducting informational interviews with people who have careers you admire.

Keep the end in mind.

It is challenging to plan for the long-term, but it helps to have a mental image of the kind of life you want to build.

Work and life are not separate entities. Work is part of life. Try to visualize where you want to live, the kind of person you want to partner with (or if you even want a partner), and how you want to spend your time on a daily basis.

I knew I wanted geographical flexibility because I wanted to help young people navigate their careers, not only in India, but also around the world. I wanted autonomy over a strict daily schedule. I wanted to master how students and early career professionals learn and unlearn. I wanted to create a job that gave my future self a deeper sense of purpose.

While I could have indirectly made an impact in the career navigation space at Microsoft, I knew I wanted a more direct connection with the people I was trying to serve. Committing to Network Capital full time would give me that opportunity.

Pro tip:

Write your future autobiography. Before leaving Microsoft, I actually sat down and wrote a sort-of autobiography. I reflected on what the most defining events along the way would be. I was intentional about describing (in great detail) what I wanted to be remembered for and the way I spent my time. Eventually, how you spend your time is who you become. Conducting this thought experiment gave me more clarity on what mattered most to me and why. This doesn't need to be 100 pages long, but it does need to give you an idea of what you want your journey to be.

WHAT (do you want to do)

Assess yourself.

While some may know already they want to work in another industry or go back to school to learn something new, many don't know what their next step should be. But it is impossible to know where you are going if you don't know where you are. The simplest way to conduct this self-assessment is to ask yourself these questions:

  • What's my end goal?
  • If I keep doing what I am doing today, will I get closer my ultimate goal?
  • Will my 80-year-old-self have more or less regrets because of my current choices?

After that, write down the steps you will need to take to make your future self proud and the problems that you might encounter in doing that. An important part of learning where you are is in understanding the challenges that are keeping you there. Then, look at the list of things you need to do to get closer to your goal. Find, know, or strike out challenges you have no control over.

For me, one issue that I couldn't control — at least in the short-term — was income predictability. Would I make an equal amount of money at Network Capital as I did at Microsoft? Would I need to change my lifestyle? On average, corporate compensation is significantly higher (at least in the early days) than the income one can expect in early-stage ventures. Complaining about it or worrying about it obsessively would have been a waste of time. If quitting got me closer to my goal, and I chose to pursue that goal, how would I work around this problem?

I came up with a plan inspired by Wired co-founder Kevin Kelley's concept of 1,000 True Fans. Kelley advises:

 "1,000 true fans is an alternative path to success other than stardom. Instead of trying to reach the narrow and unlikely peaks of platinum bestseller hits, blockbusters, and celebrity status, you can aim for direct connection with a thousand true fans. On your way, no matter how many fans you actually succeed in gaining, you'll be surrounded not by faddish infatuation, but by genuine and true appreciation. It's a much saner destiny to hope for. And you are much more likely to actually arrive there."

I gave myself the target of getting Network Capital 1,000 monthly paying subscribers over a period of 12 months. I built a strategy around how I would bring in money, gave my goals a real structure, and was able to increase our number of loyal, engaged subscribers over time.

Pro tip:

Approach your self-assessment with awareness, curiosity, and a willingness to experiment. Author and entrepreneur Marie Forleo says, "Everything is figureoutable." When it comes to career transitions, there isn't a formula per se. Experimenting, tinkering, and figuring things out is the way forward.

WHEN (will the change happen)

Expect multiple rejections.

Unfortunately, most career transitions and hiring processes rely heavily on past experience. For example, suppose you are a technology sales manager who wants to break into trading or hedge funds. 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, when I was looking to transition from corporate strategy to business development, it turned out to be much more challenging that I had thought. After approaching peers on dozens of teams, I realized that very few wanted to take a bet on someone with a different experience. Finally, one hiring manager gave me a project to work on. I performed well on that project and got the opportunity to interview for his team. After eight months of trying relentlessly, I finally made the internal transfer happen.

Pro tip:

Thankfully, you don't need everyone to take a bet on you. Just one will do. Finding that person/hiring manager/recruiter will take time. Expect multiple rejections before you do. If your resolve and preparation is strong enough, you will get someone to take that chance.

Be realistic.

Some transitions are unlikely in the short-term. Don't set yourself up for failure by setting unrealistic goals in unrealistic timeframes. We overestimate what we can do in one year and underestimate what we can do in 10. You can change your industry, your function, and your geographical location but all three are unlikely to change immediately. Gradual change is often much more sustainable.

Please don't take my suggestion of being realistic to be at odds with dreaming big. Both can coexist with the proper timeframe. Dream big and act small by trying to take micro-steps in the right direction.

My first micro-step was setting up a minimum viable product for Network Capital in the form of a Facebook group, and observing two things: customer behavior and my own interest level in figuring out the messy challenge of career exploration for millennials. Without this micro-step, Network Capital would have remained an idea in my head.

Pro tip:

Micro-actions compound over a period of time to deliver exponential results. Take the first step and be consistent about it. Urgency in actions, and patience with results, will serve you well.

Have a backup plan.

Create an alternative you can live with when things aren't going as envisioned or planned. It might be somewhere in between your ultimate aspiration and your current state. This can bridge the skill and network gap you might be facing during career transitions. More importantly, it will set you up on the journey you wish to embark upon.

Today, my backup plan isn't going back to corporate. I have, however, thought through various scenarios for Network Capital. Perhaps it will become a hyper-scalable big tech company, perhaps it will evolve into a more niche offering. I am comfortable with both outcomes as I now realize I am more in love with the problem of career navigation than the solution. Hopefully, I will help solve it. If not, I can help others figure it out.

Pro tip:

Set a timeframe. Suppose you want to transition from law to social impact consulting and making that switch is proving to be difficult, perhaps because of lack of relevant experience. Here your backup plan could be time-bound. You could 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 if it still interests you.

…

Career transitions are like Shrek. They're complex and there is usually a lot more to them than we see on the surface, so you'll need to unpack the layers one at a time. For me, transitioning from the corporate lifestyle to that of a scrappy entrepreneur has been both challenging and rewarding.

I still remember my last day at Microsoft, the day I went back to office to submit my badge, laptop, and corporate expense card. I was giving up a big part of my identity. As I took a walk across the empty floor bidding adieu to all the wonderful memories and learning experiences, I knew my time here had prepared me well for the journey ahead.

If you aren't thinking about a career transition today, some day you will. As and when that day comes, my hope is that you approach it with curiosity, conviction, and commitment. Career transitions are messy, but they can also turn out to be catalysts in shaping a future self you will be proud of. There is no way of guaranteeing success, but not trying might just leave you with regrets.