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Should I Stay or Take a New Opportunity? Seeking Advice!

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Should I Stay or Take a New Opportunity? Seeking Advice!

Hi everyone,

I’m at a career crossroads and could really use some guidance. I’m currently at a startup where I’m learning new skills and working with a great team. The CEO is very hands-on, which has its pros and cons, but the company is facing financial uncertainty, including a lawsuit and ongoing efforts to secure funding. Naturally, I’m concerned about long-term stability.

Before this role, my previous job went through an acquisition, which left me needing to find a new opportunity. A mentor I deeply respect helped me land my current job, and I feel incredibly grateful for her support. Because of that, I feel a strong sense of loyalty to her, and I don’t want to disappoint her by leaving too soon.

Recently, I received a new opportunity through another trusted recommendation, with higher pay and a potential opportunity for more stability.

However, while this new company may be a bit more stable, there are still some uncertainties, including leadership changes, organizational changes, and financial restructuring. My worry is that I might be moving from one unstable situation to another, just with a slightly stronger footing.

A major concern for me is job security in the long run. If I stay and my company doesn’t secure funding or faces financial issues this year, I could find myself out of a job. At this stage in my career, I also know that ageism can make it harder to find another role quickly if I end up back on the job market unexpectedly. Which is very stressful when you are the only financial family provider.

I’d really appreciate any advice or shared experiences. Thanks in advance for your help!

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  1. Barb Hansen

    As someone who has spent years in startups and has also been the sole financial provider, I completely understand the weight of this decision. That pressure is real. Here’s my perspective:

    Loyalty to your mentor vs. loyalty to yourself: Any experienced executive understands that you have to make career moves that are best for you. A great mentor would support your growth, not expect you to stay in a situation that isn’t serving you. Staying out of loyalty alone is not a good reason to stay.

    A hands-on CEO is normal: Most startup CEOs (and early team members) are deeply involved—it’s the nature of startups. Unless their leadership style has become toxic, I wouldn’t use this as a deciding factor.

    The legal and funding situation is a bigger concern: Lawsuits aren’t unusual in startups, but if the company is struggling to secure funding and facing legal challenges, that can make investors wary. What stage is this startup in? Early-stage companies (pre-seed, Series A) facing lawsuits + funding struggles can be a major red flag for long-term stability.

    Always Be Looking (ABL): In startup land, you should always be open to new opportunities. Network with customers, colleagues, and investors—you never know where your next role might come from. I worked with the same CEO and CTO for 10 years across four different startups and building new startups with past colleagues is very common, so keep those colleague connections alive even after you've left the startup (if you decide to leave).

    Neither option is risk-free, but one may be the better bet: Startups are inherently uncertain—funding dries up, economic conditions shift, acquisitions happen, and roles disappear overnight. Right now, you know your current company is struggling. The new opportunity also has uncertainties (leadership/financial restructuring), but does it present a stronger path forward? Dig into the details—how well-funded are they? What’s their long-term outlook?

    At the end of the day, trust your gut. If the new opportunity feels like a step up in stability and pay, it may be worth taking the leap. If not, keep looking while staying put.

  2. Anonymous

    Thank you so much!

  3. Barb Hansen

    I'm always open to chat if you a sounding board if you want to dig into the outward indications of a startup in trouble.

  4. Anonymous

    If you want more stability ordinarily I would say take a government job but not these days! Find the purpose for the work you love to do. 3 things should make your decision: stability and long term potential (matters most to you), culture and career growth, and compensation. If you are in sales compensation is number #2. Either way if those referring parties are truly trusted mentors, their guidance when you share your feelings about things with both will validate the choice. See who offers up the most empathetic response that is not selling you one way or the other. The answer may reveal in those conversations. Good luck.

  5. Anonymous

    Always do what's best for you. Your mentor would want that. Keep in mind that as long as we're working for other people, there is no security. You make the best choice you can based on the info you have at the time.

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