Hi Jennifer,

Thanks for taking questions.  I would love some advice on how to figure out what interests me so that I can determine what career to pursue. 

I fell into the law after working a few jobs out of college but not really knowing what I wanted to do for a career.  I’ve hated it since day 1 and, now 15 years in, I fear the law is going to be a life sentence! 

I handle regulatory compliance and mergers and acquisitions for telecommunications companies. I hate the subject matter because it’s very technical, constantly changing, and hard for me to ever fully understand or gain a sense of mastery. 

And finally, I’m an introvert and hate the business development, conference speaking, etc. aspects of my position. 

I’ve wanted to leave the law for a long time but I have no idea of what I want to do.  I went to law school at 30 and I’m a single mom of 2. Now at age 50 I have no hobbies or friends and I have absolutely no idea of what job or career would interest me or that I realistically could pursue at this point.  

I don’t feel that my skills transfer readily to other careers and I don’t want to go in-house to a telecom company.  I enjoy doing things where I can see immediate results, and listening to productivity and personal finance podcasts.  

I don’t see how I can turn those interests into a career and I just feel stuck.  

Thanks for letting me vent.


Uncertain Future

Dear Uncertain,

I applaud your desire to figure out what work would be interesting and rewarding for you. That’s a big step for someone who lurched into law and stayed with it for 15 years despite loathing it.

But, during those 15 years you ignored, stuffed away, and silenced your inner voice. Without that voice to guide you, you’ve missed out on important cues about what lights you up and makes life (including work) worth living.

young white woman drinking whiskey from glass and holding cigarette
Image by Thorsten Frenzel from Pixabay

Right now, your inner voice is bitterly hunched in a corner on her millionth cigarette, with a bottle of bourbon at hand. (Hopefully it’s Angel’s Envy, my favorite.) She’s a hardened cynic by now, and she isn’t going to believe your interest is genuine. Initially, anyway.

She has a point, after all. No one likes being ignored, especially not for a couple decades. So to get her to talk, you’re going to have to woo her. A lot.

Listen to the Voices in Your Head

The first step is simply get your inner voice talking. You’ll need to show up consistently, listen deeply, and act upon what you hear. 

Say you suddenly, urgently want to live in the middle of nowhere—pay attention. Maybe don’t pack up that second and bolt, but don’t automatically swat that notion away as impossible or impractical, either. 

Instead, honor it. Rent a cabin in a remote vacation spot. Or make plans to go hike/hang outdoors away from people. The important thing is action; simply agreeing, mentally, means next to nothing to your inner voice.  Show your inner voice you are taking her seriously.

Embrace the Crazy 

Spend a couple months, minimum, on paying attention to your “crazy” longings, and indulging them as much as possible.

As you are doing this listening and indulging, keep notes:

  • What pops into your head that you want to try/be/do? (Do not self-edit)
  • What does the full vision of that look like?
  • What did you do?
  • Rate how you felt before you did it (1-10).
  • Rate how you felt after you did it (1-10).
  • Would you want to do it, or something like it, again?

The point of this phase is not to discover what you want to do with the rest of your life. You may get lucky and have that epiphany, but that’s a bonus at this stage. Your initial goal is to tune into your inner voice, and trust that what it wants will benefit you as a whole person. 

You will get to the epiphany part. Trusting your inner voice’s guidance will get you there faster.

At the end of a couple months, you and your inner voice should be on decent speaking terms. Plus, your stress level should be declining.

Use a Really Big Net

What comes after this initial part of getting in tune with yourself again? Keep doing more wooing. Then also start looking at non-lawyer job ads. 

man repairing large blue nets
Photo by Harry Piqué on Unsplash

If you’ve stayed intrigued by productivity podcasts, for example, maybe you look at ads for corporate training or consulting companies, or any other place that highly values productivity. 

Cast your net widely. Think about jobs and industries that don’t necessarily have the label of your new favorite obsessions, but do contain their function. People who enjoy teaching, for example, perform that function in non-profits, in training new employees, and in leadership development, to name a few. You can get even more ideas of what jobs require the function you want in your work at https://www.onetonline.org/find/, a brilliant little site developed by the Department of Labor.

This is idea generation time. Right now, you’re looking for ads that pique your interest, regardless of pay, location, or any other logistical concern.

Bright Shiny Objects: YES
Clenched Body: NO

Notice what draws your attention. Notice what makes your stomach or shoulders clench. The jobs that make you clenched or depressed, or that you are talking yourself into considering? Stop entertaining those as ideas for your next gig. I don’t care how well they pay or how much sense they make on paper, because for YOU, they don’t make sense.

At the same time, you need to talk to people about your ideas and their experiences. Yes, even if you’re an introvert. Bear in mind that one person’s story isn’t the entire truth about a job, industry, or your prospects in it; it’s a data point. Make sure you gather many of those before you decide anything.

Plus, you need a tribe of people that likes some of the things you do, and who have a similar mindset. You know, like friends. Showing up regularly to do things you like with nice people is a good way to find some tribe members, and gain perspectives that lawyers usually lack.

The Right Stuff

Most importantly, worry about the practicalities of a new career (pay, location, transferable skills) only after you’ve identified the direction you want to head. Otherwise, you’ll end up in a situation much like your current one: You make the money you want and have the “right” skills and experience for the job, but it’s a terrible fit for your soul. 

field notes phone sharpies
Photo by Kari Shea on Unsplash

Once you know your direction, then you can start considering the nuts and bolts of how to get there. Identify your ideal job(s). Then compare your current skills, experience, and knowledge base with what those jobs ask for. (Also: You don’t need everything on the list. Promise.)

Instead, use your problem-solving moxie.

Ask yourself, and others, how you can get the items you lack?

  • take an online class?
  • make connections you need through volunteer work?
  • find a job in your current industry that would give you experience you need to make that jump?

You had a life before law school, and you’ll have a rich and wonderful life after law, too. Once you’re back on speaking terms with your inner voice, you’ve totally got this.

Jennifer Alvey is a recovering lawyer and advice column addict. She has made connections at crafting classes that led to actual paying freelance gigs. 

What’s your most pressing question about changing your career? Send it to jalvey@jenniferalvey.com. Or, if you want a personal consultation, you can email Jennifer to set that up.