Should I stay or should I go?

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That uncomfortable feeling … A self assessment of when to consider a job change. I spoke to a friend yesterday, who asked for some advice. It seems her sales job wasn’t going as well as she had hoped. She wasn’t making enough money to cover her expenses, and she was “starting to feel uncomfortable”. Feeling uncomfortable is our internal warning system.

Remember the Robot from “Lost in Space”, who would announce “Danger, Will Robinson!” We all have that Robot inside us, that internal gauge that tells us if everything is good, or not. But how do we tell if this bad feeling is temporary, or something that we can overcome? My friend has a dilemma that many people see in their career. She had moved 4 months ago to a sales role, after 3 months of training. On one hand, she’s getting negative feelings from her boss….On the other hand, she’s only been in her new role for 4 months. New and heavily commissioned salespeople often struggle and feel this way at the 90 day mark, and don’t start seeing results for 6-12 months, depending on the company/product/service. Veteran salespeople know that the start-up phase of a new job is challenging. Should I Stay or should I go?

If you’re in this situation, should you stick it out? Or should you listen to your feelings and get out? The answer depends on the kind of person you are, and your specific situation. Ask yourself these tough questions:

1. How uncomfortable are you (scale of 1-10)?

2. How concerned that you are about to get terminated?

3. Do you perform you best under pressure, or do you perform best when comfortable & confident?

4. How is the stress affecting your health? Your sleep? Are you getting sick more often?

5. How is the stress affecting your relationships? Family?

6. Are there insurance or benefits reasons (Ex: education, pension, vesting, stock plans, etc) that are overriding reasons to stay at your current company?

7. Are there other reasons that leaving would be difficult? (Ex: Flexibility, lack of relevant jobs in your area, commute, daycare/school proximity)

8. How much financial cushion do you have?


9. Is your company profitable? Hitting its revenue and profit numbers?

10. Is your company hiring, holding headcount steady, or expanding?

11. Are you hearing company messages about growing sales, or managing costs?

12. Is your company seeking to be purchased, to purchase/merge with other companies, or stable?

13. Is your boss’ job stable? Is your boss under pressure, or considered a key player?

14. If your boss makes you feel uncomfortable, does he/she do this to others on the team? Or is it just you?

15. Has your boss taken away some of your responsibilities (or accounts)? Are you still in the loop for communications or meetings, or do you feel left out? Has this changed recently?

16. What have others in your company done in your situation?

17. What have you seen when others were terminated within your company? How long had the problems been going on before termination? How far in advance were formal warnings given?

18. How likely will your boss get promoted or leave? Can you outlast your boss?

19. Would you want to get transferred to another department within your company? How likely & how quickly can you get transferred?

20. Large company vs. Small? Liability and regulatory concerns faced by large companies often make it a longer and harder process to fire employees. If you’re in a small company, especially if your boss is the owner, termination decisions are typically driven more by emotion than policy/procedure.


21. What’s the job market like? Do you think it will be better, or worse, 6 months from now?

22. How transferrable are your skills? What’s your realistic estimate of how long your search will take?

23. Do you want to stay in your current field/industry? Or do you want to change?

24. How prepared are you for a job search? When was the last time you updated your resume?

25. How much time do you have to search for a job while continuing work in a pressured environment? Some overall thoughts: Reasons to stay: If you haven’t had any two year job tenures in a while, consider toughing it out. It is even more difficult if you were at your current employer less than a year and leave without a couple of success stories. Employers discount “bouncy” resumes, and judge job hopping candidates as having less adaptability to tough situations. If you feel you’re handcuffed to the company due to benefits, you likely have a challenging decision.

Reasons to go: You usually have a job search advantage if you make the decision to leave, before possible termination (Exceptions: Long severance packages, really bad job market conditions, no relevant jobs in area). It is more difficult to confidently explain why things didn’t work out, in a way that makes you look good. Even if your company had layoffs due to losses, employers often view this as poor judgment on your part, especially in management roles.

If the job market is good now, strike while it’s hot (it won’t be hot forever). If you are being asked to do things that are unethical or illegal – go. Period. Either Way: Get your resume ready, and start networking, just in case. You never know what kinds of great opportunities are out there until you open yourself up to the possibilities. And it’s good to be prepared.

Phil Rosenberg is President of reCareered. If you'd like more information, a free 30 minute resume consultation, or information about reCareered's new Teleseminar series, please visit and we'll schedule a time to talk.

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