Alternative Career Jump: When to Say Goodbye

When you’re looking to make the jump to an alternative career, there’s never going to be a moment where a wise old man says “it’s your time.” In the real world, you have to make decisions and follow through on them. If you’re thinking of leaving Big Law because there’s something else you think you should be doing, my best advice would be to start planning now. There’s not much of a blue print for people trying to leave the law and do something else, so I’m trying based to pass on some lessons (a few painful) that I had to learn.

Save as much as you can

Step 1: Save, save, save. This is the biggest mistake people make when they leave big law for a lower-paying career. Whatever you think you may need or have, double that. If you plan on leaving BigLaw and you already know that now, start cutting costs ahead of time. The obvious ones are house/apartment and car. If you live in a fancy lawyer apartment, move out now and downgrade. Break your lease if you have to, the money you save will be staggering. Not only will start immediately saving hundreds or thousands per month, you will start acclimating yourself to the lifestyle you are choosing. Trust me, it’s not gonna be as fancy for a while. For me, I foolishly stayed in my West Village apartment for almost 6 months after I left BigLaw. I could have stocked away a decent chuck that I certainly could use right now.

Is your alternative career already providing income?

Are you already making income from the job you’re switching to? For me, I knew it was time, partly because I was actually starting to get paid for my comedy and writing. If you’re not making money from your alternative career, then it might be wise to continue working at law firm until you have some money coming in from your new job. For one, it will allow you to transition better, but it will also give you some sort of realistic sense that this new career is feasible.

Start building your network in your new field

It takes years to build the relationships you need to be successful as a lawyer; it’s no easier in other professions. Give yourself at least 5 years before you can really reap the benefits of whatever new venture you’re attempting. It may be more or less, but that seems to be a benchmark that many people I’ve talked to use. Think about your career as a lawyer. The first couple of years, the learning curve is steep, but then it levels off and you get to start seeing the big picture, plotting a career path. In my comedy career, I am now about 5 years in and starting to finally see some dividends. I left BigLaw 2 years ago, but was doing comedy part time for 3 years before that while working full time in the law. Those few years allowed me to build my comedy career to a point where I had connections and a portfolio of work so it wasn’t just a leap into a new career that I would have to start from scratch.

Don’t completely cut the cord

Your friends and colleagues from BigLaw can be an invaluable resources. Everyone kind of roots for the guy that got out, so to speak. In my experience, my biggest fans have been the friends I made while working at my law firm. Also, you may find out that you don’t really want a new career, but just needed to scratch an itch. The time off may give you a new perspective on the law. I knew a guy at my old firm that left as a 7th year to pursue acting. A year later, he came back and realized he actually was content being a lawyer and is now a successful partner. It happens a lot more than you’d think. And even if you don’t go all the way back, you can and may need to return to the law either as a document reviewer contract lawyer, freelancing, legal blogger, etc. So obviously don’t be the guy that sends that bridge-burning email.

When you know, you know

Notwithstanding everything I just said: you will know it’s the right time. Even if you haven’t done all of the above things, you may just have a burning desire to chase your alternative career dreams. All of those things above were meant to be helpful tips, not to discourage. Absolutely go for it, if your heart and mind is telling you that your calling lies elsewhere.



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  • Great perspective and advice, Matt. Some good life lessons in here no matter the journey you choose: plan ahead, realistically; know it takes longer than you think (for most things); and keep up your relationships

  • Good piece. I left Biglaw 10 months ago to do something entrepreneurial. Still very much TBD whether it’ll work out. I agree with all advice above. Just like to reiterate how important the points in “Don’t completely cut the cord” are.

    (1) I happen to be doing a law-related software startup and happen to like a lot of the people I knew from my law days, but even if neither of these things were true, my law relationships would be very valuable to me now–I’ve really appreciated being able to call super high-quality lawyers for area-specific legal advice (which you could easily need) and unsurprisingly law people know other people, and these other people can be helpful in your new area.

    (2) Current and former lawyers would like you to succeed in your new role. As Matt says, “Everyone kind of roots for the guy that got out, so to speak.” I’ve found even random lawyers I meet on a flight are interested and curious about what I’m doing now.

    Again, useful and good piece.

  • Matt Ritter

    Thanks for the positive feedback. I really do think having left the law over 2 years ago, I’m still learning lessons everyday about how to do it in a way that can help you the most.