Choosing a Path You Can Convince Yourself is Right


My coaching clients come to me knowing what they want to do--they have a career and job search target in their sights. What they need is help reaching those targets. But what if you don't know whether you should be looking for a new job or a new career? What if you're not sure what type of work environment you should be in? What if you're thinking that maybe law school and life in a law firm are big mistakes?

That's where Chelsea Callanan comes in. She's the founder and president of Happy Go Legal. I've asked her to share her thoughts on finding the right career path and her new coaching tool to help lawyers find the right fit.

- Shauna C. Bryce, Esq.

Choosing a Path You Can Convince Yourself is Right

Guest Post by Chelsea Callanan

I talk to numerous lawyers a month who are facing major hurdles in the career and professional development. One of the areas that I hear a lot of concerns about comes from lawyers who have been out of law school 1 to 6 years, who are trying to figure out if they are on the right career path for the long-term. Maybe they are in private practice on the associate track and not positive they want to stay where they are to become partner. Maybe they accepted their first job out of school out of desperation and want to make a change before they are pigeonholed in a practice area they don’t enjoy. Maybe they are burning out, and wonder if it’s them, or if it’s the job.

If I were to make a very high level assessment, I could likely categorize the major challenges into two categories: 1) I think I need to change jobs, and 2) I don’t know what will be a better fit for me. The foundation of both of these very real challenges is uncertainty. “I think” and “I don’t know” are very frustrating and scary reasons to consider making a major life and career change. It’s what I did twice, leaving jobs to try something new, because I didn’t know what I actually wanted. I was trying to find “greener” pastures, without first deciding what “greener” meant to me. If you are in a state of wishy-washiness, of feeling like you aren’t satisfied in your career but aren’t sure why, it can lead to lots of sleepless nights, anxiety, and guilt.

Selling Something You Aren’t Sure Of

Any good salesman will tell you that you will get better results in sales if you believe in what you are selling. I encountered how awkward it can be to sell something you aren’t sure of two years ago, when I was interviewing for my last law firm job before pursuing self-employment. I had been working with my sister to win a business plan competition to open a business in our hometown, and it just so happened that a local print publication ran a cover story about our win and the competition the same day of my daylong interview with 15 attorneys at the law firm.

Guess how many times one of them asked me – “so what’s with this other business?” or “do you want to work at a firm or run a business?” Guess how convincing I felt saying that I definitely wanted to work at a law firm, when deep down I was so uncertain about what I really wanted. I did feel strongly that I wasn’t ready to abandon the hopes of finding a law firm job that felt right, and wanted desperately for this job to fill the gaps I had felt in past positions. But in hindsight, I can see that I squelched my excitement of where my entrepreneurial endeavors might take me, to stay the safer course. It wasn’t intentional, and I regret any harm my lack of certainty caused any of my former colleagues, but I was selling something I just wasn’t sure of.

Before you cast a wide net to try to find a new job that may or may not be any better in the long run for you – consider whether you are convinced of your future career path. Before you put yourself into a situation where you need to be selling yourself to a hiring committee that their job is the perfect fit for you (while a desperate voice in your head is really just hoping for any change that will be better), let’s consider how you could change this story a bit.

Why Finding the Right Path is Harder than You Might Think

Law school teaches us to “think like lawyers” which is good and is also bad. Thinking like a lawyer to issue spot claims, be able to research effectively, and write concisely is good. Thinking like a generic lawyer – who is often more in touch with what everyone else’s needs are than their own – is bad. Lawyers are trained to be risk-averse, to mitigate damages, and to keep the client’s or partner’s needs at the forefront. We look to precedent cases to predict what will happen in our case, to sway the judge, to negotiate down towards what we really are willing to accept.

So when lawyers have no idea what it is that would make them happy, or are hard-pressed to confidently write down six-month and five-year goals for their career that excite them, it is no big shock to me. A law degree provides a very versatile degree, even if it doesn’t feel like it at first after graduation. But you need to be willing to actually think about what you want out of your career, to decide what “greener pastures” look like for you. Sometimes when people think they need to change jobs, they are just trying to avoid one particular personality conflict in the office rather than learning communication tactics to work through it. Sometimes when someone doesn’t know what would be a good fit for them, it is because they just accepted “a job” out of school, to pay the bills and start working without knowing what they wanted. They didn’t have a longer term plan that they were working towards with particularity.

This is why I work hard to create and vet resources that help lawyers become more in tune with their own priorities, goals, needs, and strengths. I am passionate about helping other lawyers find their right career path, more successfully and quickly than I did. If you fall into this category of wishy-washy, unhappy for “some reason” lawyers – consider taking this challenge on and create an action plan to find your right path sooner rather than later. Maybe you are on the right path and just need some mentoring, or maybe you really are at a point of needing to start a job search.

Instead of navigating these waters alone, consider working with me, and a group of other lawyers, who are in the same boat. Happy Go Legal is offering its first ever Right Path Group Program, aimed at helping you utilize resources and books that compliment my coaching style, to make some big decisions, that could benefit the rest of your life and career. Even if the group setting isn’t for you, there is also a Right Path Laser Assessment that might be more up your alley. Interested in learning more? CLICK HERE – the Group Program starts September 17, 2013 and has limited seats, so act now! And because I love the Bryce Legal community, enter Discount Code HGLGroupPath to receive $20 off whichever program you feel is a good fit for you.



BIO: Chelsea Callanan is a practicing lawyer, blogger, and career & life coach – she founded her company - Happy Go Legal - to provide resources and education to inspire lawyers to prioritize professional development and work-life balance issues. Her number one suggestion to lawyers is to take time to identify what it is they are working towards, and what achieving it will mean for their life. Only then will you find success and sustainability. Hear the rest of Chelsea’s story about how coaching changed her life and career and consider whether it’s time to take your career into your own hands.