Thinking About a Mid-Career Switch to Real Estate? 5 Things You Must Understand First

If you are considering a mid-career switch into real estate, you are not alone. With headlines frequently discussing the “Great Resignation,” many professionals are rethinking their careers and long-term security.

In the corporate world, you might have built some skillsets that can be brought over to self-employment.

For instance, you have excellent interpersonal skills, good salesmanship and perhaps some digital IT skills.

Here are five important considerations to reflect on before making the leap, based on insights from Stuart Chng, Executive Group District Director at Huttons Group, who has spent more than a decade building and managing real estate teams.

#1. Get Your Finances in Order First

This step cannot be rushed.

Before leaving a stable salaried role, you must take time to plan your finances carefully. If you are married, have an open and honest discussion with your spouse—especially about how household expenses will be managed during the transition.

Like starting any business, real estate requires runway. Income is not immediate.

Beyond personal living expenses, you will also need to cover business-related costs and start planning for the standard costs of being a real estate agent:

• Licence renewal fees

• Property listing subscriptions (e.g. PropertyGuru, 99.co, EdgeProp)

• Marketing and advertising expenses (e.g. flyers)

• Transport and fuel costs

• Digital marketing expenses such as websites or online ads

  
  

Commissions are typically paid four to six months after a deal is completed, so cash flow management is critical.

Before you resign, calculate how much savings you need to comfortably get started.

Find out how much is required to begin.

#2. With Great Freedom, Comes Great Responsibility

One of the biggest changes in self-employment is how time suddenly feels abundant.

You no longer report to a boss. Your schedule is yours to manage. But at the same time, there is no longer a guaranteed monthly income.

Deep down, many people make the switch because they realise that relying on a single income source can be risky in today’s world.

Choosing self-employment means taking full ownership of your financial future—both the rewards and the risks.

If this idea has been on your mind for a long time, it may be a sign that you are mentally preparing for entrepreneurship.

#3. Letting Go of Your Old Identity Is Harder Than You Think

After spending years—sometimes decades—in the corporate world, job titles can become part of how we define ourselves.

But a title is simply a label. It does not describe your character, values, or how much you care about others.

Many people struggle because they subconsciously equate their worth with their previous position.

This makes it difficult to step into a new identity.

In real estate, the core identity you must embrace is service.

Yes, you are technically your own boss. But to truly succeed, you must see yourself as someone who serves clients, listens deeply, and adapts to their needs.

You may have been used to giving instructions in your past role. Now, you must be open to receiving feedback—from clients, prospects, and even your team leaders.

If you stay open to learning and are willing to apply what you learn, you will be well on your way to becoming a capable and trusted property agent.

Find out your possible routes of advancement

#4: You Must Be Willing to Keep Showing Up

I once knew a high-achieving corporate professional who left behind a six-figure income and a prestigious title to become a property agent—largely due to health and personal priorities.

She could no longer sacrifice her well-being for corporate expectations.

Eight years later, she enjoys a healthier work-life balance, and her income has surpassed what she earned previously.

What she remembers most, however, was the initial rejection.

Former colleagues stopped returning calls. Messages were left on “read.” It was discouraging and painful at first.

But she stayed consistent. She continued sharing value, stayed humble, attended training, improved her marketing, and took on even small rental assignments to gain experience.

Over time, her sincerity became clear. Some who initially ignored her eventually became clients and referral sources.

She kept showing up—day after day—and that consistency built a sustainable business.

To this day, she still thanks her first few clients annually, grateful they believed in her when she was just starting out.

#5. The Right Mentor Makes a Big Difference

Transitioning into self-employed real estate is not easy.

You will need an experienced leader and mentor to assist you in growing your real estate business. You are not just changing jobs—you are reshaping your identity.

I can assure you there will be growing pains. You might be outfoxed by sly competitors or prospects who play you out. There will be people who will take advantage of your lack of experience or assertiveness.

Having an experienced mentor or leader is critical. There will be moments of doubt, difficult prospects, and competitors who test your boundaries.

Sales is frontline work. You will experience highs and lows.

But with the right guidance, you will learn resilience, sharpen your expertise, and discover how to create your own opportunities.

With the right platform and support, real estate can become one of the most rewarding and fulfilling careers available today.

Do you have what it takes to lead a team?

Final Thoughts

If you ask me what being a real estate agent truly means, my answer would be this: it is a journey into entrepreneurship.

Entrepreneurship is not just about skills—it is about beliefs, character, and personal growth.

Your business will ultimately reflect who you are becoming internally.

That is why this path is one of the most powerful forms of personal development.

You must be willing to struggle, fail, learn, and take action—even when everything is not perfectly figured out.

Instead of waiting for the ideal moment, you learn to build the parachute on the way down.

The income you earn over time is simply a measure of the value you create.

If you are seriously considering a mid-career switch into real estate, schedule a complimentary 30-minute career consultation with Stuart and his team leaders to explore whether this path is right for you and get your questions answered.

Now may be the time to take that first step.

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Stuart Chng, Executive Group District Director of Huttons Asia, is a renowned leader and personality in the real estate industry.

He adores music and can play a few instruments decently without upsetting his neighbours. When not doing so, he enjoys pillow fighting with his son and coming up with silly puns which barely amuses his wife.

Professionally, he is a licensed real estate agent, an avid stocks, options and real estate investor, multiple businesses owner, team leader, speaker and columnist for several property newsletters and blogs and is often quoted in media interviews on 938FM, Channel 8, PropertyReport, PropertyGuru and other publications.

Throughout his career, he has helped many clients grow their wealth through selecting great property investments and managing their portfolios actively. Read his clients' reviews here.

Stuart has also coached many top million dollar producing agents from top real estate agencies in Singapore. Read his agents' reviews here.