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CHAPTER 3

KEEPING OR LEAVING YOUR DAY JOB

You’ve probably noticed that people are embracing entrepreneurship like never before. Due to the widespread availability of technological business tools, there’s never been a better time to become your own boss. With an internet connection and a smartphone or laptop, you can work from just about anywhere on the planet.

While there’s nothing wrong with holding down a W-2 job and getting a steady paycheck, having income from your own business comes with many upsides, which we covered in the previous chapter. But if you’ve been dreaming of quitting your day job to start a business, you might be wondering if taking such a big leap is worth it.

The good news is that there are incremental ways to become self-employed that are stable and reduce your risk, instead of plunging abruptly into a precarious financial position. In this chapter, you’ll learn practical strategies for building a solo business while keeping the security of a regular job. Since doing both for an extended period (or even a short one) may stretch your limits, I’ve also included some essential tips for creating smart work habits and getting more done in less time.

Tips for Building a Business on the Side

Becoming your own boss may seem glamorous from the outside, but it can have stressful pitfalls, such as little pay, no insurance benefits, and unpredictable clients. However, you can avoid or minimize some of the downsides by maintaining a reliable day job while you grow your solo business. Having the security of a job and the excitement of becoming a solopreneur gives you lots of upside with much less risk. A steady paycheck may give you the confidence you need to take business risks—such as buying more advertising, equipment, or software—that will make your venture more profitable.

Aside from maintaining a reliable income stream, being both an employee and an entrepreneur can make you a better worker. In my experience, growing a side business also builds skills and experiences that make you more effective at your regular job. You may even find your side hustle revives an appreciation for your day job. There’s a lot to like about having a salary, benefits, and other perks, after all.

Whether you decide to be both an employee and your own boss for weeks or years, it will take some juggling to manage successfully. Here are five tips to face your career fears responsibly and prepare for the future by adding entrepreneurship to your resume on the side.

Define Your Vision for Success

Before changing your job or making the transition from employee to self-employed solopreneur, take the time to define what you truly want to achieve in your career. Sometimes your ideas about success come from other people, and they can cause you to follow a career path that never truly fulfills you.

Maybe your boss thinks you should regularly work late so you can climb the corporate ladder, or a parent says you should go to graduate school. You might take a lucrative job in a field you’re not crazy about because that’s what your friends are doing. But if that job requires frequent travel when all you truly 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 follow other people’s priorities when it comes to your work. If your decisions aren’t purposefully leading you toward a life that excites you, you’ll likely wander away from what you genuinely want.

Never let external markers of success, such as a big paycheck or a fancy job title, become more important than your heartfelt calling and goals for your life.

That said, getting in touch with your real desires isn’t always easy, and you might have to listen carefully to hear your inner voice. Try incorporating some quiet time into your daily routine. When you first wake up or when you’re settling down at bedtime, think about what you’re grateful for—but also what you’d like your life to be. Consider your definition of success and any changes you’d like to make to your life in the near and distant future.

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

$ What type of work makes me 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 once to figure out the arc of your entire life. You need to come back to these fundamental questions during different seasons of your life and career, because the answers may change, sometimes repeatedly.

Over time, your working life is sure to change, in both good and bad ways. When you find yourself getting restless or feeling like you want more from your job, slow down and become more introspective. It can reveal a lot about what your next career or business move should be.

Create a 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. Jumping from a day job into an uncertain, full-time venture too early could mean trouble. You might face significant financial struggles and even get into debt. As I mentioned in Chapter 2, many businesses take years of hard work before they’re profitable enough to support you.

Hanging on to your day job gives you the financial security you need to try out new business ideas, especially if you have a spouse, partner, or kids who depend on your income.

The best side gigs combine work that you’re excited about with something that you’re uniquely positioned to provide. These businesses may also come with a large existing customer base or appeal to customers who are willing to pay you well for the skills and experience you offer.

I was a part-time entrepreneur for a decade before I said goodbye to my employer. I enjoyed having a mix of job stability and entrepreneurial upside. Plus, I found that expanding my career by adding self-employment to a W-2 job made me much better at both.

If you slowly add entrepreneurial experience to your career, you’re likely to gain a variety of skills that will make you more valuable to employers. It may be easier to experiment with businessformation ideas when you have less financial stress or know a side gig could actually complement your 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 financially vulnerable. 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.

Negotiate Your Job Flexibility

If you plan to start a business on the side, or you already have, you know 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 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 begin seeing increasing revenues, you may find that you need more flexibility in your schedule. At that point, consider some different ways that you can tailor your business for your day job, and vice versa.

In 2008, my employer began feeling the financial pinch of the Great Recession. My podcasting and blogging career had started to take off by that point, so 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 a week for the rest of the year. Then we’d reevaluate where the company stood and discuss whether he could still afford to keep me on as an employee.

My employer would save money by paying me less, and I’d have more time to work on creating content, partnering with brands, and writing my first book, while still having a regular paycheck coming in. If I hadn’t suggested that solution, my company wouldn’t have known that I was willing to cut my hours. I didn’t offer to tell my boss what my plans were for my newfound free time, and he didn’t ask.

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

If you have a long commute or spend a significant amount of time getting ready, packing a lunch, and getting out the door in the morning, working remotely could save a lot more time than you think. Then you can invest that saved time in your side business.

Find More Time in Your Day

If you can’t get more flexibility or you worry that even asking for it could put your day 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.

Find a nearby cafe or reserve a conference room in your office where you can work and eat undisturbed. 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 quiet or privacy in your office, you could even work in your car.

If working on your business during your lunch hour 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 in a nearby coffee shop or a co-working space (where drop-in memberships can often be had for the same price as joining a gym) before or after your job. The idea is to create a routine that builds in regular time to focus entirely on your venture and to complete essential tasks.

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

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 with a more reliable schedule. If you’re truly committed to getting your business off the ground, you may need a position with more flexibility so you can do both more easily.

Have a Solid Exit Strategy

Having an exit strategy is a common concept in the business world. Partners and investors want to know what will happen after clearly defined milestones are reached, such as taking a company public or selling it after a certain profit margin is achieved.

But employees should create exit strategies, too. It’s a great way to force yourself to think about the future and what you would or should do next. With a W-2 job, you never know what’s around the corner.

Your company could suddenly downsize after a merger or an unexpected loss of market share. Your department could be reorganized after new leadership begins. All these scenarios have happened to me at some point in my career.

It’s wise to start every professional relationship with an idea of how it could end. This ensures that you’re never caught entirely off guard. Knowing that you’ve thought about the end of a job or a business partnership can make you feel more secure about a potenti al split.

What’s Your Exit Strategy? Exercise

Imagine that you will be losing your job in three months. Answer the following questions to help you prepare an exit strategy for leaving your job:

$ What would I like to do next that’s truly exciting?

$ What can I do now to build a business that gives me an additional revenue stream?

$ Who should I connect with in my existing network?

$ What industry events should I attend to make new contacts?

$ Do I have enough savings to last for a period of unemployment that could be six months or longer?

$ What job benefits should I use before leaving?

$ How would I negotiate a severance package?

If you’re unprepared for an interruption in work or business income, it can be devastating to your emotional and financial life. So whether you’re laid off or you voluntarily quit, prepare for it now.

If you have a financial runway to find new opportunities or you’ve built an income from a side business, quitting or getting fired can be a positive experience. Having a good exit strategy can make the difference between feeling crushed by a job loss or becoming empowered by it.

Secrets to Turbocharge Your Productivity

Whether you leave a day job to dive into starting a business full time or dip a toe into a side gig, you’ll need to become a master of productivity. While this book doesn’t focus on productivity, I’m recommending some essential tips here that will help you establish good work habits and achieve a lot more for your business in less time, resulting in more profit-making potential for your solopreneur venture.

The Three-Minute Rule

This rule is an incredibly powerful way to get small tasks off your plate so you can focus on bigger ones. The idea is to complete any task or chore if you can do it in less than three minutes.

It could be related to your work or home life, such as sending an email, putting clothes in the washer, cleaning your desk, or filing something. Apply this rule to any task that needs to be done—or that’s distracting you from your work. If it would take you less than three minutes to complete, do it now.

Give It Ten

When there’s a more significant task or project on your plate, but you’re procrastinating for whatever reason, tell yourself just to give it ten minutes. If you’re like me, you probably tend to avoid tasks that you think will be complex, take a long time, or you just don’t like doing.

While you might not complete a big task in ten minutes, beginning it usually unlocks your ability to maintain momentum and get it done. Maybe you’ve heard the proverb “Well begun is half done.” That’s productivity gold! Simply getting started on a project—especially one you’re dreading for some reason—makes it so much easier to keep going.

So the next time you keep putting off work you need to do, work on it for ten minutes. You might use a clock or timer on your phone to keep track. You have permission to stop after those ten minutes are up. But you’ll usually keep going once you realize the task is easier than you thought or that it’ll take less time than you anticipated. Taking action by getting started can unlock a world of achievement.

Match Tasks to Energy

While everyone gets the same 24 hours in a day, the quality of those hours varies considerably. Your energy level throughout the day depends on many factors, including your sleep and wake cycles, known as your circadian rhythm.

Pay attention to your body and notice when you’re tired and when you’re most alert and thinking clearly. You might notice that you have a dip in energy at the same time every day. Whenever you’re most alert is when you should be working on what you value most. If that’s your budding business, carve out that slice of time to focus on it.

For instance, if you’re a morning person who works a day job and a side business, get up a little earlier to knock out some business tasks before you head to the office. If you’re spent mentally after a full workday, the evening might be the best time to exercise or do household chores. The reverse is true if you’re a night person.

The idea is that adjusting your life and work schedule to match your natural energy patterns will make you more effective and efficient at everything. In reality, we only have a few peak hours per day to fire on all cylinders, so don’t waste them on low-priority tasks. Save your errands, chores, and physical activity for times when you’re not as sharp mentally.

If energy-matching is a new idea for you, begin observing how easy or difficult it is for you to complete different tasks. When you feel challenged, instead of pushing yourself to continue working, try doing the task at a different time of day. You may get it done faster and with a better attitude.

For example, although I usually wake up early, I wouldn’t say that I’m a morning person. After getting up, it takes me a while to feel completely alert. So I prefer doing my high-priority and high-focus tasks, such as writing or project planning, in the mid- to late morning. By then, I’ve had some coffee and gotten a few low-priority chores out of the way. By mid- to late afternoon, I usually don’t feel as focused, and I’ll turn my attention to administrative tasks, errands, and exercise.

Trying to fight your body’s clock typically doesn’t work. So use your natural energy rhythms to your advantage and schedule work that matches it.

Schedule Everything

Speaking of scheduling, that’s another critical way to get more done. Schedule everything in your paper or digital calendar. When you have your entire day mapped out, it’s easier to stay on track and avoid distractions.

I even put taking a shower, cleaning out my junk mail inbox, and engaging on social media in my digital calendar. For me, if it’s not on the calendar, it doesn’t get done. To make scheduling easier, you can use the repeat function to set up any recurring tasks that you don’t want to forget.

Knowing that everything you need to do is centralized in one place can give you incredible peace of mind. To stay on task, remember that your job is to focus on and complete what’s in your calendar. And if you finish ahead of schedule, you can begin the next most crucial item, turn to an easier item, or take a break.

And speaking of breaks, be sure to schedule those, too. Whether you want to eat, mindlessly surf the web, or take a walk, breaks boost productivity. My favorite way to rest my mind and reduce stress is to listen to short podcasts or chapters from an audiobook.

Delegate More

The most effective way to boost your productivity is to delegate or outsource tasks that someone else can easily do. For example, I have a virtual assistant who helps me with communication, graphic design, and social media outreach. My goal is to focus on the core business tasks that I do best and enjoy.

Letting go of tasks isn’t easy, and it may make you uncomfortable. If you’re a control freak, like me, you probably believe that no one else can complete a task as well as you. And you may be right.

So begin delegating slowly. Also remember that in many cases, getting low-value tasks done quickly, but not always perfectly, is better than having them pile up on your plate. Plus, outsourcing creates opportunities for your fellow business owners.

Stop Being Busy

Have you ever heard of Parkinson’s law? It’s one of my favorite adages because it’s so true. British naval historian and writer Cyril Northcote Parkinson wrote in 1955, “Work expands so as to fill the time available for its completion.”

Consider making it your computer screensaver or putting it on sticky notes where you work. It’s a great reminder to stop keeping yourself busy with low-value tasks and start doing work that matters.

I’m sure you’ve been in a situation where you procrastinated doing something for days or months, but somehow pulled out all the stops and completed the task just ahead of a looming deadline. If something must be done tomorrow, you’ll get it done tomorrow. If you have a week, you’ll take a week. You may not have more time than anyone else, but you can often use the time you have in better ways.

However, don’t try to get more done by multitasking. You really can’t focus on two things at once, especially high-value tasks. It’s much better to focus entirely on one thing and do it well than to complete several things poorly.

Check in with yourself throughout the day to see what your energy level is and whether you’re being productive or just busy. If you’re not solely focused on the most valuable task possible for your business, switch gears quickly. Focus on high-value tasks by setting strict deadlines, scheduling them in your calendar, and getting to work!

All the tips we’ve provided in this chapter can help you balance your day job with your side business, but only you can decide when it’s time to leave your job. In the next chapter, we’ll cover how to ease the added financial pressures of becoming a solopreneur so your transition is as smooth as possible.