Can I leave a foot in the door as I swipe out for the last time?

Dear VGCB:

Interesting dilemma. Not the first time I’ve heard of bankers (or, for that matter, lawyers and consultants) who dream of leaving to pursue their passion but want to know they can still come back if it doesn’t work out.

I will be honest: there’s no going back. You’re buying a one-way ticket.

If I understand you correctly, you want to tell your boss that finance isn’t your cup of tea, but still leave the door open to a return in case you don’t have success and need the money.

I can’t imagine any employer prepared to hire you back unless they are desperate or have a secret crush on you.

Of course I understand what you want to do. You don’t enjoy the work, you dream of a different career path, but you don’t want to be left with no money and no job if the new venture doesn’t pay off. But I’m afraid that in life (as in Brexit) you can’t always have your cake and eat it too.

As I’m sure you know, investment banking is ultra-competitive, both internally and externally. When you leave, the organisation fills your seat pretty quickly. Juniors move up, peers move across, and any gap is quickly taken. The next generation of juniors arrives in the autumn, and the Lion King-style circle of life continues.

Moreover, it’s really hard to absorb a mid- to senior-level banker who has been away for a few years. It’s disruptive even in the best of climates. I’m sure you can find the odd exception, but in every case that banker will have had a niche skillset, a unique client relationship, or something extraordinary in their track record. Assume you are not this unicorn.

I’d even say that if you try to negotiate a way back as you are giving your exit notice, senior management will conclude that you’re flaky, unfocused, and even a bit self-indulgent. You will garner little sympathy from them. They will respect you more if you show that you are going all-in on your new career. Conviction is compelling; hedging your bets isn’t.

In other words, when you leave the institution, you should assume you are on your own. The safety net is taken away.

And remember: the odds will be running against you. I don’t know what artistic endeavor you’re intending to pursue, but most of the arts have a much more extreme power-law distribution than investment banking, in which the top 1% (or maybe top 0.1%) capture the economic rents and leave scraps for everyone else to fight over. You’d be like bright-eyed Betty (played by Naomi Watts) in Mulholland Drive who goes to Hollywood to become a movie star. As the movie shows, she is fantasising the whole time — she’s really Diane, a struggling actress unable to land meaningful roles and consumed by murderous envy.

I’m not saying your experience will be as lurid, but you should skip the fantasy and focus on the reality: you will likely achieve meager success in whatever arts you choose. You will probably run through and run down your savings unless you have a family trust fund to backstop you. These may be risks you’re happy to assume given your passion, but you should make an informed decision.

So here’s the way I’d think about it:

First, you need to slow down your burn rate. You say you have two years of financial runway. I’d downsize significantly and slash your living costs now so that you give yourself more time. Two years is a blink of an eye. You need at least four years to give it a realistic try.

Second, you should channel your inner Hernán Cortés. The explorer famously scuttled his ships in Veracruz in 1519 to foil any plans of desertion or retreat by his men. You have to do the same, at least mentally. Not just because you will likely have no job in banking to return to, but also because artistic success requires uncompromising commitment. There’s no room for half-measures. You have to go all-in; this isn’t a two-year sabbatical from finance, but rather a wholesale exit.

Third, act professionally on your way out, but don’t make a big scene. Nobody is interested in hearing a manifesto about why you find finance unfulfilling or why you’re pivoting to the arts. Say goodbye, be gracious, wish everyone well, and just say you’re leaving to pursue a personal venture. Sure, you should keep in touch and maintain your network, but don’t delude yourself into thinking they will hire you back.

So... once you run the numbers and review the odds, do you still want to leave finance? If so, then go, and good luck. Life decisions are all about accepting trade-offs, and this is no exception. Just make sure you know what you’re getting yourself into, and don’t have any illusions or delusions along the way.

Best,

Craig