Considering a career move? Start by asking these 8 questions

Bigger. Better. Bolder. Inman Connect is heading to San Diego. Join thousands of real estate pros, connect with the Inman Community, and gain insights from hundreds of leading minds shaping the industry. If you’re ready to grow your business and invest in yourself, this is where you need to be. Go BIG in San Diego!

During a career, there often comes a moment — not marked by burnout or dissatisfaction, but by a quieter, more persistent realization: You may be ready for something new. Perhaps your current role no longer challenges you, or the work that once felt fulfilling now feels routine. Maybe the industry is evolving faster than your current environment can accommodate.  

These signals can be subtle. According to a recent Career.io study, real estate professionals report high job satisfaction, rating their job a 4.24 out of 5. Yet, paradoxically, the industry also ranks among the top three for burnout, with professionals changing roles approximately every 3.91 years, according to 2024 research published by PsychologyJobs.com.

This duality underscores the complexity of career decisions — you can be passionate about your work and still recognize the need for change.

So, how do you know when it’s time to make a move? I spent 30 years affiliated with my previous company before joining Coldwell Banker. Three decades. That transition wasn’t driven by dissatisfaction — it was the result of thoughtful reflection and strategic consideration.

In today’s dynamic real estate landscape — characterized by market recalibration, economic volatility and uncertainty, industry consolidation and rapid technological advancement — proactive decision-making is not just advantageous; it’s imperative.

Recently, I had the pleasure of meeting with Anywhere Real Estate’s Rising Star award winners. We discussed ways to advance their careers and navigate changes that may be inevitable. Here’s my framework of eight key questions to help guide career decisions.

Whether you’re contemplating a move or simply reassessing your path, these questions can provide clarity:

1. Are you clear on your purpose?

Time is one of our most valuable and limited resources. In your professional journey, it is essential to have a well-defined vision of how you allocate your time and with whom you choose to invest it.

Consider focusing not only on what you wish to achieve or acquire, but more importantly, on who you aspire to become. Aligning your actions with a clear sense of purpose will drive more meaningful and impactful outcomes. 

2. What are your core strengths — and where do you need to grow?

Conduct an honest self-assessment. Identify your key competencies and areas for development. Too often, individuals change their external circumstances without first addressing the internal changes necessary for meaningful progress.

Then ask: Do you want to deepen your expertise or broaden your skill set? And, consider whether your current organization provides the environment and resources to support that development. 

3. Have you engaged in meaningful career conversations within your company?

Before looking outward, look inward. Speak with your manager and cross-functional leaders. Explore potential opportunities within your current organization that align with your goals. 

4. Do you understand your financials?

Evaluate the true cost of each transaction — both in time and money. Without a clear understanding of your financial metrics, it’s difficult to assess whether a new opportunity offers real value or just better marketing. 

5. Are you speaking with the right people?

Don’t rely solely on recruiters. Engage with individuals across all levels of the organization you’re considering. Culture fit is critical — without it, even the most attractive compensation package can feel restrictive. 

6. What’s holding you back?

Change is emotional. When I made my move, it felt like choosing between loyalty and betrayal. Acknowledge those feelings, but don’t let them paralyze your progress. Often, your peers will support your growth more than you expect. 

7. Who will support you through the transition?

Transitions involve many moving parts — branding, licensing and onboarding. Have you met the team that will guide you through this process, or are you relying on promises from leadership?

8. Is this about FOMO?

With so much movement in the industry, it’s natural to feel as though you might be missing out. However, not every opportunity is the right one. The key is to evaluate alignment in timing and opportunity. If the timing is right but the opportunity is not, the outcome may be unfulfilling.

Conversely, if the opportunity is compelling, but the timing is not, it may still lead to disappointment. Sometimes, the wisest decision is to stay the course. After all, the grass tends to be greenest where we consistently water it. 

Recruiting efforts will continue. The industry will keep evolving. But your next move should be driven by vision and intention, not pressure.

Take the time to reflect on where you want to be in two, five or 10 years. Whether you choose to stay, pivot internally or make a bold leap, ensure your decision is strategic, intentional and aligned with the professional you aspire to become. 

Jason Waugh serves as president of Coldwell Banker Affiliates for Coldwell Banker Real Estate LLC.