Taking the First Step as a Career Transition

I think it is just beginning to dawn on me how significant of a step I took when I decided to leave my job at Goldman. I’m a year and half into my P.F. (post-finance) life and, for a variety of reasons, it’s just hitting me now. It seems sufficient time has passed such that the public has deemed me beyond the point of no return and they are starting to marvel at my apparent insanity. I’ve been asked with increasing frequency: “How did you do it? How did you figure out how to leave and not look back?” There’s also the fact that my bank account is dwindling and I’m marvelling at my own apparent insanity. I still don’t regret it for a second, but the reality of changing my lifestyle has certainly settled in.

Additionally, as the buzz around the startup community in Hong Kong grows, I am talking to more and more people who are working in finance, consulting, or other corporate jobs, and secretly dream of one day leaving to pursue some other passion. Though many credit money for being the primary reason for not taking that leap, I think it’s something else — or at least a combination of factors. For me, it was both a lack of direction and a lack of confidence in my own abilities. I thought, if I did leave my job … what is that ‘other’ passion that I would pursue? I have always been interested in a lot of different things, but I never had that one thing that I loved so much or that I couldn’t live without. I am not obsessed with one industry, one product, one activity that would make it glaringly obvious what I should pursue.

And from a practical standpoint, what would I even be able to do? I’ve always been kind ofgood at a lot of different things, but never excelled so much at one thing that I had no choice but to go after it. If anything, my strength would be general business skills, which is why I dream about starting or running a company one day. Even still, the only jobs I had in my adult life were… bank teller, smoothie/sandwich girl, tour guide, a little data entry, and Equity Derivative Sales. Not really the most applicable background if you want to start a company.

When I would share this frustration with people, their answer was always, “Why don’t you just go to business school? You can figure it out there.” But I didn’t want to take two years to go to business school to “figure things out.” My frustration with my then position was that I didn’t feel like I was really doing anything. It felt like I was just spinning my wheels every day. If I went to business school, I was only delaying the inevitable. It wouldn’t actually solve my perceived lack of productivity.

I really believe this is a fundamental desire that lies within every one of us. A desire to break free of our constraints and get to a place where we can truly contribute, where we can build something bigger than ourselves, where we actually matter. It is natural to seek the satisfaction that comes from seeing tangible results of something real that you did, an idea you came up with, connections that you made — that satisfaction is indescribable. I think it’s fundamental because it means you have a sense of agency — the ability to contribute, to create, to choose is precisely what makes us human. So, I suppose it’s ironic that so many of us are waiting around for someone to tell us it’s okay to take control of our lives and to make a conscious choice to be free. We don’t actually need to rely on other people to get a taste of creation. It’s ours for the taking, we just have to go after it.

So, then, how did I get started? It didn’t happen overnight. But, even though I had no idea where I was going to end up, I did take some small steps to set myself on a different path. Here are some little things I did that I’d recommend for anyone lusting after a change. These seemingly minor changes are what allowed me to subtly, passively, subconsciously formulate my escape plan.

1. Expose yourself to your other options in the corporate world by signing up for notifications for job listings. I had never looked for a job outside finance, I had no idea what was even out there. There’s a lot of riff raff, but at least you’ll have a sense for your “practical” alternatives and the skills/background they would require.
2. Sign up for Escape the City. This was first thing I signed up for after all the traditional newsletters. Getting exposure to non-traditional options will open your mind and help you consider something you’d never even thought of before. I didn’t think I’d move to sub-Saharan Africa to work for an NGO, but who knows? It got me thinking out of the box.
3. Make sure you subscribe to both of these things using your PERSONAL E-MAIL. Or, maybe don’t, and your employer will find out and make your choice for you.
4. Beef up your LinkedIn profile. Add your experience, your background, ask for recommendations. This puppy is pretty powerful and recruiters spend hours trolling for candidates with certain backgrounds. You never know who might reach out to you. I got my first startup interview for a role at ZocDoc after someone randomly contacted me through LinkedIn.
5. Talk to your friends. Tell people you trust that you’re looking for a change and that you’re unhappy. If you’re still unhappy and complaining years later, they’ll hold you responsible and subtly push you to make a change (if they’re good friends, that is).
6. Start writing cover letters and doing interviews with start ups or other random industries you’ve vaguely been interested in. Telling you now, you probably won’t get the job (I got lots of rejections before I joined GA) but you’d be surprised how much value you get out of talking about your skill set, listening to how you sell yourself to others, testing how far you’re really interested in taking things. That way when the right thing comes along, you’ll have a clear picture in your head of why you want it and how you can contribute.
7. Sign up for Meetup.com, commit to some random activities, and meet some people in different industries. Try out some new things, listen to other people’s paths and stories, expand your realm of possibilities. It’s so inspiring to meet other people who are passionate and eager to share their interests.
8. Go to a class or sign up for a course at a place like NYU School of Continuing Ed or General Assembly (I’m not just saying this, I’m serious. I did this before I worked there). You’ll gain a practical insight into other industries, you can make some solid connections with the instructors and other leaders in the field, and perhaps most importantly, you’ll get exposed to other people that are searching just like you are. You may think you’re special — and you probably are — but that doesn’t mean you have to be alone. Because the reality is you’re not alone. There are so many other people out there looking to make change but aren’t ready yet, or don’t know how yet. There are also a lot of people out there that have made the change, and they’ll make it seem a lot less scary.
9. Get involved in a project, whether it’s through friends, through a hands-on/project-based course as mentioned above, or even through Craigslist. It doesn’t have to be your own, it doesn’t have to be your dream passion project, but you’ll get to exercise your mind, test and come to understand your own capabilities, and you’ll feel amazingly empowered to see that you can accomplish something meaningful out of your office. It will remind you what human agency tastes like, and you’ll have no choice but to go looking for more.

So, there you have it. It’s a long list, but it’s pretty easy to do. It won’t force you to do anything you’re not ready for, but it will help you passively prime yourself for success. You’re just warming up your muscles for your leap so you don’t sprain, tear, or break anything. Before you know it, you’ll find yourself at an impasse where it feels natural to just jump. I can tell you from experience, it will still hurt, but as long as you’re properly prepared it’ll be a really good kind of sore.