Lessons I Learned During the Scary Business of Changing Careers

Learning to embrace the unknown was a lot of work.  Learning to accept that it would be uncomfortable, scary and difficult seemed impossible and was a major exercise in patience and self-trust.  My life was going to be different and I had to learn to be excited instead of frightened. 

This summer marked 11 years since I quit my job as a corporate lawyer. 11 years. A good friend of mine who only knows me since I moved to the Hudson Valley and was already focused on painting and photography full time, recently told me that she could never imagine me in an office behind a desk reading and analyzing documents all day. So much has happened in that time - including a brief return to corporate life after I had my second child - but I can honestly say that I’ve never been happier even though the ride to this station in my professional life was, at times, very bumpy, very unclear, and often very terrifying. I’m grateful for the time I had to learn things the hard way even though I couldn’t see how important that was at the time that I was learning.

So what do you do if you want to change careers? It’s scary for sure but here are some lessons I learned.


I wish I understood then that it was okay to not know how things were going to turn out.  It's not as though I knew where I would end up when I decided to go to law school in the first place but I simply could not get my mind to go back to that place where I just lived my life, worked toward a goal, and let things happen.  It's okay if you don't know what your goal is right away, the important thing is to recognize that it's possible to achieve it once you figure out what "it" is.


2.  Your current job is not necessarily your life-long career.

If you hate what you do, keep reminding yourself that there are other possibilities and educate yourself on whatever else is out there in terms of a possible career change.  Take the time to read about other potential careers.  When I finally decided I was ready to quit I had been in such a rut that I wasn't able to see this.  My career change was more clear cut because I had a passion that was more than just a hobby but it’s helpful to think about your lifestyle, what you like, what motivates you and what makes you tick to get closer to figuring out what is best for you. Once I actually became a "corporate dropout" I met so many other people who were like me and who made a change in careers and left a comfortable job to try something else. 


In my case, while I felt challenged by what I was doing, there was something that was missing.  An important lesson that I learned, and that maybe I knew all along but it was buried deep inside of me with the rest of my common sense, is that things that make us uncomfortable are often what motivate and inspire us most.  Things were good because of the money but the long hours left no time for me to do anything but work and sleep (sometimes).  It was not for me.  There was something better but I just had to take the time to realize it.  This was an honest conversation that I had to have with myself.  I wondered how my personal life could be so great but my professional life so not and I realized that if I was that unhappy in my job eventually it would affect other areas of my life. 

4.  Ask yourself: What am I good at?  What inspires me?  What was I doing at a time in my life when I felt happy and fulfilled?

This is more of a tip rather than a lesson. Think about these questions and make a list of your answers.  The answers might lead you to your next career. I educated myself as much as I could and it made me feel more confident and less afraid.  I’m still learning!  I approached switching careers and learning about switching careers as a job in and of itself.

5.  Be realistic.

I was a lawyer who was looking for a creative outlet.  I started to pick up my camera more and more to get back to the hobby I loved.  But just because I had a camera and knew how to use it didn't mean I was a photographer.  I had no false expectations about what I could do because I had no clue what I could do.  I still have no false expectations and I try to take it day by day. I also knew that the change was not going to happen overnight.  Now I just try to focus on my end goal and I try to organize and be efficient with my time splitting my day between full-time working artist and full-time mother. I stay in my lane and just worry about what I have to do to get my work done and my vision out there. I try to be realistic about what I can achieve in a certain time frame and practice patience knowing I won’t be able to balance it all (like, it’s actually impossible so I gave up trying). 


Plus, I just told myself that if it didn't work out it did not mean that I was a failure (it took me a while to really believe that).  I could always go back to being a lawyer but I had to try to do the something else that I was craving.

6.  Think of a plan and write it down. 

It doesn't have to be a business plan or anything too formal at first.  I started by making a simple spreadsheet and a raw timeline for myself.  Items on my spreadsheet included stuff like a projected budget, ideas for a website, a list of people I could reach out to and network with, hiring a designer, researching jobs.  My husband is a spreadsheet guy and he helped get me started by encouraging me to talk it all out. Some things were in granular detail, others were more general.  The spreadsheet went through several drafts and it made me think harder about what I wanted to/could do.  Once I saw it all written down it helped me to visualize it more.  My ideas were no longer just in my mind and it started to seem more real and possible that I could make a change in careers.  If a spreadsheet is not for you, make a flowchart or just start a list that is more a stream of consciousness than anything else.  The point is just to start!

This assumes that you know what you want to do.  If you have no clue other than to know that you want out of your current situation, making a plan is still helpful.  Write down what inspires you and what your interests are and go from there.

7.  Use what you have to get what you want.

Whatever it is that you're doing now is not a waste.  It's a learning experience!  Leverage your current position to help you into the next one.  As soon as I started to see my situation as an advantage to get me to where I wanted to be, I felt more positive and sure of myself.  I took a part-time job working in my family's real estate management company in order to make some extra money while I was making the transition.  As a licensed attorney in New York I was able to obtain my real estate broker's license and working in an office a few days a week helped me feel like I still had my foot in the corporate door while giving me more time that I needed to properly research the career that I really wanted as a photographer.

Everyone wears so many different hats.  I joke that my title is "Professional Juggler" and as a mother, artist and creative, that’s definitely the case.  I’m not a career counselor - I'm just someone who has gone through this before and I'm learning every day how to be better.  There are a lot of people like me (and there’s comfort in knowing that)!  I even went to law school with a guy who was an anesthesiologist interested in medical malpractice law!  If you start to ask around and really talk to people, you will see that changing careers is actually really common.  And, you might also find that people who have gone through this are super receptive to questions and are willing to offer whatever advice they have.

I have some days that are better than others.  I often still feel insecure and unsure of myself.  The type-A person in me has learned to accept rejection and has learned to tolerate that scary feeling of not knowing what is going to happen next.  It's not as scary anymore.  Most days I feel excited and inspired and yes, I feel proud.  

These are things that worked for me but everyone's experience is unique!  There are simply no clear cut, easy answers.  I wish there were but as with anything else, you just have to see where life will lead you.

If you’d like to read more about my experience going from corporate lawyer to working artist, you can check out this interview.
