Trie Advice: Should I Stay Or Should I Go?

As a writer, career coach and an adjunct professor at Indiana University teaching two career success preparation courses, I get asked several excellent career-related questions all the time. You may have some of the very same questions as the ones I get from clients, students and readers, so I’ll start sharing them regularly on my blog.

Some questions merit straightforward responses such as:

Do I really have to network? (YES)
How many references do I list on my resume? (none)
When it comes to a job offer, what’s negotiable? (everything)
When should I create a LinkedIn profile? (yesterday)

For more complex questions, often the more powerful response is a combination of guidance and an invitation to reflect on some key questions I pose. In these cases, my role isn’t to tell them what to do but to guide them and help them nurture their own ideas and thoughts in a creative, focused and productive manner. So in effect, sometimes my advice comes in the form of encouraging people to look inward for the answer.

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Today we’ll tackle a very common yet complex question I hear in some form from individuals in all career stages, whether they’re in their first job right out of college or 20 years in: “Should I stay or should I go?” Let’s look at one woman’s situation.

Dear Trie ~

I’m 33 and have been working as a researcher in a law firm for 5 years. I enjoyed this job for about a year before it started becoming extremely monotonous and it became clear there really was no room for advancement. I stayed for awhile because the pay is pretty good and it was already my fourth job out of college. But now I’ve stayed so long that I’m used to how things are and I’m afraid to leave and have no idea what else I want to do. Any suggestions? Thank you, Emma M, Chicago


Dear Emma ~

First, thank you for reaching out, and congratulations on taking the first step toward considering new possibilities! It’s understandable you have some fears about leaving a position that is familiar and provides steady, solid pay. The really good news is that it sounds as though you don’t need to make any quick moves.

Now, the short answer: Whether you stay or go is entirely up to you; I invite you to close your eyes and picture how you will feel one year from today if you haven’t left your current job or found a way to enrich it. And remember that exploring career change doesn’t commit you to a career change, and you can proceed at a pace that suits you.

Now, my wordy response: Before you start drafting your letter of resignation, I encourage you to be sure you’ve fully explored any untapped opportunities at your current workplace that might provide you with new challenges and enrichment. I’ve seen many individuals breathe new life into their work merely by having a great conversation with HR or their boss about ways they could add value to new projects; take on a new leadership role; mentor other employees; or shift their responsibilities in order to allow them to focus more on their core genius.

If those conversations have happened or you’ve determined that’s not the path you wish to take, consider spending some time figuring out what you’d rather be doing in regard to: what your ideal workday would look and feel like; what skills and talents you have that you’d like to use more; how much income will be necessary to meet your goals and how to position yourself for a new job or career.

Knowing there’s a process to finding a career you will love and that there are specific actions to take in a particular sequence tends to provide some calm and comfort to individuals who feel stressed and uncertain about career change. Since you are in your fourth job, it may be that you’ve yet to discover what you’re most passionate about and what type of work you do really well and enjoy doing. There are several good skill assessments you can take to get the process started, including 16 Personalities, The Big Five Personality Test and CliftonStrengths Solutions (formerly StrengthsFinder).

number 1It’s also important to look inward and get clear on your personal mission, top goals and values so you have a good sense of how your top skills can best be utilized. I will send you a set of questions and activities to help you kick off this Discovery phase, which is Step 1 in my career transformation process that’s helped hundreds of people find work that makes them thrive.

I encourage you to dream big and really get clear on the type of work that would excite you and truly make you eager to start your workweek (as in Love Monday!). Consider what you want your work and your life to look like 5 years from now; 10 years; 20. Think about what you want your legacy to be. That vision and positive energy will steer your career transformation process and determine how far you take it.

Best wishes to you and stay in touch to let us know how your journey progresses!
~ Trie

P.S. If you would like my take on your career matter, email me at!


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