Thinking of Leaving Investment Banking?
Read This First

You are three, maybe five years into a career you were once thrilled to enter. You are good at it—genuinely good. Your work product is clean; your reviews say “high potential,” and yet, somewhere in the last eighteen months you started writing a resignation letter you have not sent.

Question One. Before you send it, answer one question honestly. The answer determines whether leaving will fix anything: Are you tired of the “work,” or are you tired of a “bad version of the work”? Those are different diagnoses, and they do not share a cure.

I have interviewed tons of people who wanted out of their job, their industry, their career, and I learned to listen—to hear—past merely the words. When a candidate tells me the hours are brutal, I learn nothing—the hours are brutal nearly everywhere the work matters. When a candidate tells me the work is meaningless, I have learned everything I need to know.

Question Two. So, ask yourself the second question I ask them: What is the part of your current job you would not miss for a second? Not what is hardest—what would you not miss?

If your honest answer involves the craft itself—the analysis, the negotiation, the judgment, sitting across a table from a Founder or Family Business owner at the most consequential moment of their professional life—then go. Truly. Find work you love, where you’ll be valued and appreciated, and don’t let anyone in this industry make you feel small about it.

However,  if your honest answer is a list of things with nothing to do with the craft—e.g., the fourth revision of a page no client will read, the pitch you knew you would never win, the sponsor you spent a decade pandering to, the fact that you have not been alone in a room with a decision-maker in eighteen months—then you are not finished with investment banking. You are finished with an institutional, bureaucratic version of it!

What Actually Got Taken From You? You entered a profession built on relationships, trust, and judgment and instead were slotted into a function built on volume and process. You were told client contact would come with the next title, and then the next one. You learned to optimize for deal count, league-table credit, and the logo on your business card, because those were the things your environment could measure. And the further you got from the person whose life the transaction actually changes, the less any of it meant.

That is not your personal failure; it is a structural one. A firm with thousands of professionals cannot run on individual judgment—it runs on specialization and process. But specialization is insulating as well as theoretically efficient.

A Different Set of Values. We work exclusively with successful Entrepreneur Owner-Managers™—founders and families who built something significant, usually once, and who will sell it once. They care deeply about who the next majority owner can be. There is no repeat business to protect and no fixed fee for turning a crank—rather it’s one owner, one family or founder, and a decision that makes a massive positive change in the rest of their lives—for them, their families, their employees, their communities. That changes the physics of your career. We are practitioners of our craft who are called to work exclusively with Entrepreneur Owner-Managers™.

Here, you own the responsibility for the whole deal, not a slice of it. You will build the model, make the call, run the diligence, and have the awkward conversation with the seller’s spouse—the one nobody staffs, yet the one that quietly determines whether the transaction closes at all.

No one assigns you work. There is no staffer, no playbook, no class year. The people who thrive here can tell you immediately what they would do in their first ninety days if nobody handed them a task.

You will be argued with, out loud. This is an intense, passionate team where ideas are contested in the open and seniority does not settle a question. If you have never told a senior person they were wrong, in a room, in front of other people, this will feel like conflict. It isn’t. It is how we reach the right answer.

The credit and the consequence are both personal. When it goes well, everyone knows whose work it was; the same is true of the other case. Most frustrated bankers think they want the first half of that sentence. The ones who belong here want both halves.

Who This Does Not Work For. I would rather be helpful than persuasive to you, so let me be equally direct about the people who do not fit here.

If you draw your identity from the institution’s name rather than the work, you will genuinely miss it here — a real loss, not a character flaw. If you measure a career in title cycles and visible peer benchmarks, we do not have the ladder to give you. If your counterparties have always been institutional agents, then the emotion, ambiguity, and family dynamics of a founder-led principal will be much, much harder than you expect.

If you need training or a program, we are not built to provide one; this is a scrappy boutique firm for people who already have meaningful M&A advisory experience from a Wall Street or strong middle-market firm (and often an MBA). And if you are optimizing purely on the number, or cannot commit to the geography, say so in the first conversation and we will both save a month.

The Question That Separates. There is one interview question I keep returning to, and you can ask it of yourself tonight without speaking to anyone.

Tell me about a client in whose life you helped bring about massive positive change.

Watch what happens in your own head. Some people answer with a transaction: the size, the multiple, the process, the tombstone. Others get animated and start with a human being—what they were afraid of, what they wanted for their children, what they said at the closing dinner.

Both answers come from capable professionals. Only one of them belongs in this work.

If you got animated, you have not lost your Unique Ability®. You have been working somewhere that has no use for it. That is a solvable problem, and solving it does not require leaving the profession.

Before You Send the Letter. For most of my career I have watched this industry lose great people for the wrong reason. They did not leave because they stopped caring. They left because the only version of banking they had seen made caring irrelevant, and they were too honest to keep pretending otherwise.

The best candidates I meet are the ones who admit they came close to quitting. That admission is not a red flag. It is the most reliable evidence I get that a person knows exactly what they want and exactly what they will no longer tolerate — which is where a career measured in decades and relationships begins.

So don’t send the letter this week. Answer the question first. If you are tired of the work, go, and go with our best wishes for your future success. But if you are tired of a bad version of the work, there are firms—small, loud, fueled by purpose—where the job you originally signed up for is still the actual job.

We are one of them, and my email address isn't hard to find. If you contact me, I will make sure you get connected to my colleagues at Bigelow to begin a conversation.  Email me at [email protected].

*Unique Ability® is a registered trademark of The Strategic Coach Inc.  All rights reserved.  Used with written permission. www.strategiccoach.com