Which do you hate looking at more, your estate plan or your resume?

It’s been a little quiet on my blog because I have been busy with my new side-turned-full-time hustle rewriting people’s professional resumes. Resume writing shares a common and very central theme with legacy and estate planning: narrative. Whether it’s your personal or your professional story, both are very challenging to get down in writing. Even if it’s easy for some of us to chat about our jobs and lives at the playground and at dinner parties, when we’re asked to distill what we do, who we are, what’s important to us, and what makes our stories unique, we feel overwhelmed and self-centered.

But why? In addition to the fact that self reflection (and writing) can challenging work, I think there are at least three externalities at play here:

You do it under duress.

Estate planning and resume writing are things you often do when your back is up against the wall. Maybe you're pulling out your old resume because you’ve suddenly lost your job (which is happening to a lot of people during the pandemic) or you’ve learned you’re being passed over for a promotion. Maybe you’re realizing, in our new work-from-home realities, that your job doesn’t make you that happy. For estate planning, you often tackle the project after a big (and typically stressful) life change, like the loss of a parent, or the birth of a child, or a significant change in your financial situation. Or maybe you recently watched someone else’s bad estate planning cause a train wreck in their lives and want to avoid it in your own estate plan. You're worried and under pressure, which intensifies the whole process.

You can feel constrained by convention.

I start my work with new clients by asking them to tell me stories about their professional careers -- the experiences they like talking about in interviews that can showcase their unique skills and expertise. The hard work isn't identifying these stories, although that can take some soul searching, it's distilling them into short bullet points that fit on two pages (max!). Formal estate planning can feel the same way. You talk to your estate lawyer about what’s important, who should be making decisions when you can’t, where your money should go, and trust that they will capture it with the correct legalese. And while a good, polished resume can be empowering and motivate you to apply to that job, the legal documents that estate attorneys create don't typically inspire you to take on the more personal and meaningful legacy projects, like writing legacy letters or deciding who should receive sentimental, non-monetary heirlooms.

Both have important audiences.

This takes me to my last point. Both estate plans and resumes are documents with live audiences and real consequences. Your estate plan tells your loved ones how you want your affairs and assets handled when you’re no longer able to make decisions. Your resume is a marketing tool that should convince a potential employer you’re right for the job. Not only do you care deeply about what these audiences think, you may not be physically there to translate your own words and make sure their true meaning is conveyed. You may die before you go through your estate plan with your loved ones, or never make it to that first callback so you can talk about why you're the perfect candidate for the position. 

OK, so now what? Here are two pieces of advice for how to tackle both documents:

First, it’s a really really good idea to talk to other people . You need good listeners, cheerleaders, experts, editors, and counselors. You're working with very important, very personal narrative content. And in order to ensure it's authentic and true to you and your intentions, you need to try those words out. Moreover, experts and advisors can help make sure you're choosing the right words that will have the intended effect.

Second, remember that both resumes and estate plans are living documents. They evolve as you evolve. Your feelings and passions change, you take new jobs and develop new friends and family, you live in new places and have new experiences that impact how you see yourself and the world. You have to return to these documents regularly throughout your life, and you need to do so honestly, openly, and effectively. So find a way to embrace this process and remember, it’s OK to ask for help!