« Back to blog posts

Should I Stay or Should I Go?

Category: Work

Date: March 23, 2021

Sarah Stamboulie, an executive, transition and leadership coach, joined us for a Work conversation about how to professionally start over while remaining in your current occupation or place of employment. She offered advice about how to navigate career development and proactively create opportunities within your organization, while being aware of and sensitive to workplace culture. She shared tips about how to determine your standing in the company, identify various risk factors to employment, and negotiate a higher salary and/or position.

How To Know Your Standing At Your Current Job

Performance Reviews
If your current organization has performance reviews, you can rely on these to some degree to provide a sense of how you are doing within the company; however, be sure to take any “areas for improvement” very seriously, even if they seem like an afterthought. Dissatisfied managers frequently fail to communicate the degree of their dissatisfaction in employee reviews, so you should pay attention to any signs that your manager is not happy with you and your work.

Organizational Awareness
If your manager does not conduct performance reviews or provide other regular feedback, you’ll have to work harder to ascertain how you are doing. If appropriate, do try to initiate a conversation with your boss about your job performance. You can ask, “What would excelling in this position look like?” or “If you had to pick something I could change or do better, what would it be?”

If that’s not possible, try to build relationships with reliable coworkers who can offer tips about approaching managers and who are savvy about the happenings within the company and how to navigate them. It’s invaluable to have colleagues who will tell you if you have made a workplace blunder, for instance.

And don’t forget that if you share your strengths generously (i.e. Excel, reporting, crafting emails, etc.), people will be eager to help you in return.

Different Kinds of At-Risk

Economic Factors: current events impact job security based on the economic repercussions. For example, in the past year, the travel industry, hotel chains, airlines and event companies have been at risk due to the pandemic. Additionally, low stock price and poor product or divisional performance puts your job at risk.

Situational Factors: For example, a new boss may want to bring in people from their previous employer.

Organizational Factors: Consider if what you do is peripheral to the organization and can be outsourced. Additionally, a cyclical position with busy and idle periods is more at risk than positions with steady work flows.

Individual Factors: Keep in mind, if you appear miserable at your job, very often your boss is unhappy with your performance as well.


If you are concerned that your job is at risk, and you need to increase immediate job security, start working on some important projects; ideally, ones that are cross-departmental.

If you suspect that your job will be outsourced to a firm, you may be able to negotiate a different job. Consider positions that offer opportunities for growth. Or, another option is to offer to manage the outsourcing; ask the vendor to hire your employees and arrange to manage the vendor relationships for your company, adding to your experience and making you a more valuable employee.

When negotiating for higher compensation, if you have a competing offer and are salary-driven, you can go to your boss and make the case that you are underpaid. You can also share some of your personal responsibilities that necessitate a higher salary. It is important to highlight your institutional knowledge and what a loss it would be for the company if you left. Underscore your value in an assured manner, but also clearly communicate that you are torn about the decision to leave.

Working with a Coach

Company-Sponsored Executive Coaches
Your employer is their client, so you should ask your coach what they agreed to in terms of communication and confidentiality with your company. Their level of candor depends on what they were hired to do, so they may not be able to say if you should leave but can often work with you to better your work situation.

Self-Paid Executive Coaches
You are their client, not the company. A self-paid coach can always put your interests first.

Tips & Takeaways

  • If the timing of promotions is unclear, you can ask HR, or even casually bring it up at a department meeting. Don’t be afraid to be a squeaky wheel. You’re more likely to be considered when people are aware of your ambitions.
  • Quitting without a job lined up is a difficult and personal decision, highly dependent on the particulars of the situation. If you have a desirable degree without breaks in your resume, you have more freedom to do so. If you think your job search will be challenging, it’s better to have a job.
  • The second you think your job is at risk, you should see a coach. They can help you fix the issues within your current position or assist you in crafting a proposal to your employer. They can help you find a manageable way to leave, such as working for a vendor or client, so you can leave in everyone’s good graces and preserve the relationship.

Sarah can be reached at [email protected] and 212-206-9929.

Other articles:

Neighborhood News in New York

Way of Living – News July 13, 2021 Pam Frederick joined us for a Way of Living conversation about her journey towards being the owner, editor and publisher of the Tribeca Citizen, a local news website which exclusively covers the downtown neighborhood of Tribeca, Manhattan. After sharing her reflective thought process when making the decision…

Keep reading »

How Indigenous Worldview Can Change Our Future

Way of Living – Culture & Values July 6, 2021 Four Arrows, a scholar and author, joined us for a Way of Living conversation that invited us to consider how our worldview shapes our understanding of ourselves, our community, and our global responsibility. He first shared the fundamental importance of understanding the concept of worldview…

Keep reading »

Breathing with Bryan – Take 2

Wellness – Breathing / Wellness June 29, 2021 Bryan Mirabella, a human performance specialist joined us for a conversation about how breathing low, slow and deep can transform your life, from your emotional state to your physical health. He provided guidance on how to breathe to extend lifespan and shared the biology underpinning his methods. He…

Keep reading »

Breaking Bad Pandemic Eating Habits

Wellness – Eating Habits June 22, 2021 Jiying Zhang joined us for a Wellness conversation about reexamining our daily eating habits to reboot and reclaim our health.  She shared her own, personal story of learning about her own health to recover from chronic stress and exhaustion. Then, she provided actionable tips to alter our approach…

Keep reading »

Post-Covid Home Hacks

Way of Living – Home June 15, 2021 Margarita Picone, a Client Experience and Hospitality Executive, joined us for a Way of Living conversation about confidently reclaiming our homes as we navigate how we use our space and time post-COVID. We all reemerge from COVID with this special opportunity to start over the design of…

Keep reading »

Parenting with Sanity and Joy

Way of Living – Parenting June 8, 2021 Sue Groner joined us for a Way of Living conversation about the joys and challenges of parenting. She shared her CLEARR method, emphasizing how respectful communication with your child can alter the dynamic in your home, making your child more responsible while you experience less stress. She…

Keep reading »

The Power of Notebooking and Journaling

Way of Living – Literacy June 1, 2021 Stephanie Affinito, a literacy teacher educator, joined us for a Way of Living conversation about the types, benefits, and joys of notebooking. She illuminated how notebooking is an activity that can be tailored to our interests, needs, and hopes, ultimately supporting us to grow closer to the…

Keep reading »

Entrepreneurship in the Fintech World

Work – Fintech May 25, 2021 Luvleen Sidhu, the Chair, CEO and Founder of BM Technologies, Inc., joined us for a fascinating conversation about digital banking, taking her company public, and the practices that keep her grounded. She inspired us to start over with both our understanding of banking itself and how to reframe daily…

Keep reading »

Dementia with Dignity

Wellness – Awareness May 18, 2021 Patti Wick joined us for a powerful yet sensitive conversation about managing the effects of dementia, after a loved one is diagnosed. Patti shared data as well as lived wisdom that can help us to start over our thinking about dementia itself and start over our approach with loved…

Keep reading »

Timely Tech Tips

Way of Living – Tech Date: May 4, 2021 Christopher Hobbick, an IT expert, joined us for an important conversation about how to successfully, safely, and easily start over our digital lives. He shared the details of his upcoming application for estate planning and then provided quick tips for how we can use our devices…

Keep reading »

Bibliotherapy as Self Care

Category: Way of Living – Literacy Date: April 27, 2021 Stephanie Affinito, a literacy teacher educator, joined us for a Wellness conversation about reading as a method of self care. She defined bibliotherapy, illuminated self care, outlined the benefits of reading, provided tips on how to start over our reading life, and gifted us many…

Keep reading »

Finding Hope After COVID

Category: Wellness – Care Date: April 20, 2021 Mark Shapiro, MD, joined us for a Wellness conversation about his experience with COVID as a hospitalist in Santa Rosa, California. He vulnerably shared the personal and professional impact of COVID, his own takeaways and broader advice we can all use to emotionally start over, cultivating preparedness…

Keep reading »

Divided No More

Category: Work – Integrated Self Date: April 13, 2021 Atif Iqbal, a certified leadership and personal transformation coach, joined us for an indelible conversation about bringing your whole self to work; starting over by integrating the personal identity into the professional self.  The Challenges Behind Working with Integrity  Many of us have a professional self…

Keep reading »

Picture Books Are for You, Too!

Category: Way of Living – Literacy Date: April 6, 2021 Pernille Ripp, a teacher, author and educational advocate,  joined us for a conversation about the robust merits of picture books for readers of every age. She invited us to start over our reading lives by seeking the books that satisfy our interests and curiosities -…

Keep reading »

Fifteen with Gene

Category: Wellness – Fitness Date: March 30, 2021 Gene Schafer, an athletic trainer, personal trainer, and founder of ARC Athletics, joined us for a Wellness discussion centered around simple, yet effective exercises we can do in a short amount of time. Our talk felt particularly relevant after the pandemic, which has disrupted so many of…

Keep reading »

Should I Stay or Should I Go?

Category: Work Date: March 23, 2021 Sarah Stamboulie, an executive, transition and leadership coach, joined us for a Work conversation about how to professionally start over while remaining in your current occupation or place of employment. She offered advice about how to navigate career development and proactively create opportunities within your organization, while being aware…

Keep reading »

Standing Up to Anti-Asian Hate

Category: Way of Living – Pop-Up Event Date: March 25, 2021 Soyoung Park joined us for an impassioned, vulnerable, and urgent conversation about her experience with anti-Asian hate in this country. Soyoung is a Korean-American teacher educator and a scholar of early childhood. Her presentation was extraordinarily moving, enlightening and informative. It invited us all…

Keep reading »

Humor, Seriously

Category: Work Date: March 16, 2021 We continued our Work series with an informative, hilarious conversation with Jennifer Aaker, a behavioral scientist whose research focuses on cultivating a meaningful life. She shared with us how humor is endemic to professional success, social connection, and personal well-being, and how we can foster more of it throughout…

Keep reading »

Chocolate — Sweet Indulgence

Category: Way of LivingDate: March 9, 2021 Peter Moustakerski, an absolute chocolate guru, joined us for a wide-ranging discussion about chocolate, including its long history, production details, health benefits, ethical considerations, as well as where to find high-quality chocolate on our own. He also led us through a delicious chocolate tasting, offering best practices for…

Keep reading »

Executive Search in Turbulent Times

Category: WorkDate: March 2, 2021 Gustavo Alba, an expert in recruiting and executive placement, joined us for a conversation about positioning yourself in the current job market, partnering with recruiters, and the effects of the pandemic on hiring practices. He offered insider advice and context to anyone looking for employment –   Reflect on Your Strengths…

Keep reading »

Upcoming events:


Stay Up-to-Date on Startover

Sign up to be stay informed about what is going on in the Startover community—new events, features and personal stories.