5 Ways to Keep Your Day Job While You Start a Business

Starting your own business is a giant leap of faith. Here's how to face your career fears and prepare for the future by slowly adding entrepreneurship to your resume.

Laura Adams, MBA
7-minute read
Episode #609

You’ve probably noticed that people are embracing entrepreneurship like never before. With today's technology, I don’t think there’s ever been a better time to become your own boss. If you’ve got an Internet connection and a smartphone or laptop, you can work from just about anywhere in the world.

Of course, there’s nothing wrong with holding down a day job that comes with a W2 paycheck. But having income from your own business comes with many upsides. If you’ve been dreaming of quitting your day job to start a business, you might be wondering whether taking such a big leap is worth it.

Today, we’ll cover smart, incremental ways to become self-employed. These tips will help you stay stable and reduce risk instead of jumping into the fire. You’ll learn how to face your career fears and prepare for the future by adding entrepreneurship to your resume.

  1. Define your vision for success
  2. Create a profitable side gig
  3. Negotiate for job flexibility
  4. Find extra time in your day
  5. Build financial security

Here’s what you need to know about each of these tips.

1. Define your vision for success

Before changing your job or making the transition from employee to self-employed, take time to define what you truly want to achieve in your career. Sometimes, our ideas of success come from other people. That can cause you to follow a career path that never ends up being fulfilling.  

Maybe your boss thinks you should regularly work late to climb the corporate ladder, or a parent says you should go to graduate school. You might take a lucrative job you don’t like because that’s what your friends are doing. But if that job requires frequent travel when what you really want is to start a family, care for aging parents, or spend time enjoying where you live, you’ll never be happy.

If you don’t pause periodically to reflect on what success means to you, it becomes easier to fall into work based on other people’s priorities. If your decisions aren’t intentionally leading you toward a life that excites you, you’ll wander away from what you truly want.

If your decisions aren’t intentionally leading you toward a life that excites you, you’ll likely wander away from what you truly want.

So, let's say you're on-board. You realize that you should never let external markers of success—such as a big paycheck or a fancy job title—become more important than your heartfelt calling and life goals. But getting in touch with your real desires isn’t always easy, and you might have to listen carefully to your inner voice.

Try incorporating some quiet time into your daily routine. Upon waking or settling down at bedtime, think not only about what you’re grateful for but also about what you’d like your life to be. Consider your definition of success and any changes you’d like to make in the near and distant future.

Ask yourself these questions to understand your values and get clarity on your unique vision for success:

  • What type of work makes me the happiest?
  • Where do I want to live?
  • What types of people do I want in my work life?  
  • What does a good life mean to me?

This exercise isn’t something you do you once to figure out the arc of your entire life. Careers change for good and bad. When you find yourself getting restless or feeling like you want more, slow down and become more introspective.

READ ALSO: 7 Micro Habits That Create Financial Success

2. Create a profitable side gig

Even when you’re clear about what you want, one of the fastest ways to ruin your financial future is to take a flying leap from a steady paycheck to entrepreneurship. Jumping from a day job into an uncertain, full-time venture too early could mean trouble. You might face significant financial struggles and get into debt. Many businesses take years of hard work before they’re profitable enough to support you.

Instead of willingly taking on the financial and emotional costs of being your own boss, try starting off with a side hustle. Hanging on to your day job gives you the financial security to try out a business idea, especially if you have a spouse or kids who depend on your income.

The best side gigs combine work you’re excited about with something that you’re uniquely positioned to provide. Customers are willing to pay you well for the valuable skills and experience you offer.

The best side gigs combine work that you’re excited about with something that you’re uniquely positioned to provide.

I was a part-time entrepreneur for a decade before I said goodbye to an employer. I enjoyed having a mix of job stability along with the entrepreneurial upside. Plus, expanding your career by adding self-employment to a W2 job can make you surprisingly better at both.

I found that by slowly adding entrepreneurial experience, I gained a variety of skills that made me more valuable to employers. That helped me enjoy my job more and even take some additional risk knowing that my career eggs weren’t all in one basket. I could experiment with business-formation ideas without much stress, knowing they would complement my existing career.

The bottom line is that creating a business on the side protects your income, diversifies your network, and improves your skills, instead of leaving you with less. If you enjoy your entrepreneurial work and find that it pairs well with your day job, the benefits and personal growth can really pay off.

See also: 7 Ways Having a Small Business Saves Big Money

3. Negotiate for job flexibility

If you plan to start a business on the side, or already have, you know that you’ll be working more. Perhaps a lot more. You might need to work early in the morning, late at night, or on weekends to fit it all in. That hectic schedule could stress your relationships or cause you to burn out if you don’t take some precautions.

Once you’re confident about your business idea or you begin seeing promising revenue, you may find that you need more flexibility in your schedule. Consider different ways you can tailor your business for your day job and vice versa.

Once you’re confident about your business idea or you begin seeing promising revenue, you may find that you need more flexibility in your schedule.

After my podcasting and blogging started taking off in 2008, my employer began feeling the financial pinch of the Great Recession. Instead of allowing my position to get downsized, I proposed a solution that my boss liked. I’d work four days a week for a couple of months and then go down to three days through the remainder of the year. Then we’d reevaluate where the company stood.

My employer would save money by paying me less, and I’d gain a lot of time for other projects. Now, I could work on creating content, partnering with brands, and writing my first book. If I hadn’t offered that solution, they wouldn’t have known that I was willing to cut my day job hours.

You may be able to negotiate with your employer for more flexibility. You might ask to work fewer hours, to maintain hours but work fewer days, or to work from home a day or two each week.

If you spend a significant amount of time each day getting dressed, doing hair and makeup, and commuting, working remotely could save a lot more time than you think. Then you can invest that time in your business.

4. Find extra time in your day

If you can’t get more flexibility, or you worry that asking for it could put your job in jeopardy, there are other options. One is to structure non-negotiable time for your business into your day. For instance, make a rule that you’ll step away from your desk for a solid hour, or longer if possible, during lunch to accomplish something meaningful for your business.

It’s incredible how much you can accomplish in 45 minutes if you truly focus.

Find a nearby café or book a conference room in your office that will allow you to work and eat undisturbed for a portion of your day. I did that for many years, and it’s incredible how much you can accomplish in 45 minutes if you truly focus. If you can’t find enough privacy, you might take calls from or do work in your car.

If working on your business during midday isn’t possible with your day job, consider coming to the office an hour earlier or staying later. You could also work on your business from a nearby coffee shop before or after your day job. The idea is to create a routine that gives you time to focus entirely on your venture and complete essential tasks.

Another option is to outsource a portion of your work to freelancers. If you can afford to delegate some of your business or W2 tasks, that can help you balance your to-do list.

When your day job is so unpredictable that it prevents you from working on your side gig for long periods, consider getting a different job. If you’re committed to getting your business off the ground, you may need to find a position with more flexibility so it's easier for you to both work and build your business.

5. Build financial security

Career changes can be challenging enough without added financial pressures. Without money in the bank, it can be challenging to be creative or feel justified spending time on your business.

I recommend everyone have some amount of emergency savings. Ideally, you should accumulate at least three months’ worth of living expenses in the bank. Having a cash reserve becomes even more critical if you plan to become a full-time entrepreneur someday.

If you don’t have any savings, take advantage of your day job’s steady paycheck to build it now.

Consider the worst-case scenario. For instance, you believe your side-gig is profitable enough to quit your day job, but for whatever reason, the revenue quickly dries up after saying goodbye. I can't overstate the importance of having enough financial runway to support you during the ups and downs of your business.

If you don’t have any savings, take advantage of your day job’s steady paycheck to build it now. You’ll feel incredibly empowered knowing that you’ll never be trapped in a job because you can’t afford to leave it. Cut back on nice-to-have purchases, such as shopping, vacations, and dining out, so you create financial security and increase your entrepreneurial options.

No matter if you’re thinking about becoming a solopreneur (like me), having a small business with a handful of employees, or founding a world-changing company, you have a lot to offer. It’s never too late to put your skills, ambition, wisdom, knowledge, and relationships into an exciting new venture.

See also: 5 Steps to Create Your Own Self-Employed Benefits Package


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About the Author

Laura Adams, MBA

Laura Adams received an MBA from the University of Florida. She's an award-winning personal finance author, speaker, and consumer advocate who is a frequent, trusted source for the national media. Money-Smart Solopreneur: A Personal Finance System for Freelancers, Entrepreneurs, and Side-Hustlers is her newest title. Laura's previous book, Debt-Free Blueprint: How to Get Out of Debt and Build a Financial Life You Love, was an Amazon #1 New Release. Do you have a money question? Call the Money Girl listener line at 302-364-0308. Your question could be featured on the show.