When is it Time to Quit Your Day Job and Go All-In on Real Estate Investing?

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Anyone who has tried real estate investing and loved it knows how tempting it can be to say goodbye to their day job and transition into full-time investing. While there are plenty of investors who successfully make this leap, this choice should never be taken lightly.

With plenty of planning and extensive research and consideration, you can determine when it’s the right time to transition from your day job to full-time investing and how you can most effectively make this switch.

Characteristics of successful investors

While there are certain skills and abilities you can learn and develop as you become an investor, there are other traits the most successful investors come by naturally. You can hone these characteristics over time through careful practice and intentional work, but you should be able to demonstrate these traits long before you make real estate investing your full-time job.

Risk management

Before you can begin investing on a full-time basis, you must be able to effectively manage risk. You should already understand enough about investing and the market as a whole that you can carefully weigh different options and choose investments that have the greatest likelihood to benefit you and help you achieve your goals.


It’s normal for emotions to play into some of your decisions, but real estate investors have to set their emotions aside from time to time to make pragmatic decisions. If you have a hard time separating your emotions from your decision-making, full-time investing might not be right for you.

Quantitative skills

You’ll likely spend a lot of time crunching numbers as a real estate investor. You need to have good quantitative skills and a strong ability to consider and process various facts and figures when you’re making investment choices.

Questions to ask before investing full-time

If you have the skills necessary to succeed at real estate investing, there are a few questions you should ask yourself to help you determine whether it’s the right time to make a transition from your day job into full-time investing.

It’s always risky to make a career move, especially when you’re moving from a steady job to a self-employed career as a real estate investor, but answering these questions honestly can help you get the timing right for your transition.

Do I like my current job? One of the most important things to consider is whether you enjoy your current job or career. If you’re in love with your current job and you want to advance in your career field, it might be best to hold off on a major transition into full-time investing and stick to investing on a part-time basis. On the other hand, if you don’t like your current job, think critically about whether you will enjoy real estate investing more. Investing full-time isn’t for everyone and it’s important to figure out whether you’ll be more content with investing than you are with your current position.

Can I work alone? Investing in real estate requires a lot of personal initiative and intrinsic motivation. You have to be able to chart your course and take control of your own investment decisions. While you can certainly partner with other investors and mentors to help you along the way, you have to rely on yourself at the end of the day. If you feel confident in your ability to work independently, make executive decisions and pursue new opportunities, full-time real estate investing might be the right career path for you.

Do I have the capital to make a career change? You should have sufficient savings to support yourself as you transition into full-time real estate investing. Consider what your current cash flow is from investing and determine how much you can expect to make if and when you move to full-time investing. It typically takes some time before full-time investing starts to pay off, so you should be prepared to support yourself for a while before you can bring in consistent income from your investments.

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Should you go full-time?

There’s no easy way to determine whether it’s the right time to transition into full-time real estate investing, so it’s important to take time to honestly assess where you’re at with your career and your investment portfolio. Once you finally leap, continue to assess your circumstances to help you find areas where you can improve or make positive changes.

There will always be an element of uncertainty in real estate investment, but you can take steps to minimize this risk and help ensure success.

When Is It Time To Quit Your Day Job and Go All In On Real Estate Investing? With Scott Dillingham