4 Essential Questions to Answer Before Quitting Your Job and Starting a Business


Are you excited about starting a business? Well, you shouldn’t be! Did you know that 95% of businesses fail within the first 5 years? You’re almost guaranteed to fail, and how horrible would that be?

You’ll put in thousands of hours trying to build your business while your friends get promoted and move into bigger houses…all for nothing.

Can you imagine everyone laughing at you when you’re working your ass off every weekend while they go fishing or have drinks with their friends?

How did that feel?

What was your emotional reaction to what I just said?

I know it may have been unpleasant, but I wanted to help you assess your current mindset and discover how badly you want to create a business. Your reaction to these statements will tell you a lot about both!

I’d like to give credit to Dan Lok for this fantastic idea. I knew I would need to use it some day J

Creating a business is tough and usually takes years. For the most part, your success depends on your mindset.

How much grit do you have? How patient are you? How obsessed with your vision are you? How long can you wade through the darkness without giving up? What are you willing to sacrifice?

Ideally, the first paragraph should have triggered thoughts like the following: “I don’t care if 95% of businesses fails”, I’m still going to be successful”,  “I’m going to be the 5% that succeeds”, or “I’ll keep pushing until I succeed, even if it takes me years.”

If you experienced deep feelings of insecurity and fear while reading the first paragraph of this article, that’s a sign that you’re not yet fully committed to your business.

Don’t worry too much. You can work on your confidence and prepare yourself for the road ahead. Hopefully, this article will help you strengthen your confidence and fuel your desire to create your own business.

 You’re still reading, so I assume your desire to quit your job is as strong as ever. You still want to escape the rat race and never look back. You’re ready to kiss rush hour, micromanaging bosses, meaningless tasks, childish gossip, and endless meetings goodbye. I understand completely.

Now the question is, are you ready to take the leap? And if so, how do you know it? How do you make sure that you can leave your job permanently?

Your answer to the four questions below will help you gain some clarity regarding your level of readiness.

1. Are you better at disciplining yourself than your boss is?

Many of us dream of quitting our jobs, but few of us will actually hand over resignation letters and escape the 9 to 5 with big smiles on our faces. As a wannabe entrepreneur, you must be able to answer the following key question: Can you discipline yourself better than your boss can?

If your answer is no, you might be in trouble. Quitting your job to create your own business should mean that you’re more effective and productive on your own than you are when working for someone else. It should mean that you’re confident in your ability to get things done even when there’s no one around to push you.

Perhaps you’re still unsure of whether you have enough self-discipline to work on your business consistently for months and years to come. If so, answering the next 3 questions will help.

2. Do you have enough patience and perseverance to succeed?

You may be a hard worker who is willing to pull all-nighters and work 80-plus hours a week to create your business. That’s fantastic, but you have to keep in mind that building a business is a marathon, not a sprint.

Can you sustain that pace for the next 3, 5, or 10 years? Can you focus on your business for an extensive period of time without getting distracted by something that’s seemingly more exciting? It may take years to get the results you want. Can you keep going even when you’re discouraged?

You may think you know the answer to this question, but there’s only one real way to find out. You can, and should, start your business as a side hustle. This is best for two main reasons:

  1. It will allow you to assess your level of motivation and how passionate you are about what you’re doing. Building a business is tough. If you don’t have the motivation to work on your side business before work, after work, and during the weekends, it’s safe to assume that you won’t be able to create a successful business after quitting your job.
  2. It allows you to test your patience and perseverance. Sacrificing your free time to build your business while your friends are going out or watching House of Cards can be painful. Can you stay patient when you’ve gone months or even years without much progress? Working on your side business will help you figure that out.

If you can work on your side hustle for 2 to 3 years while holding a full-time job, the odds of your success will significantly increase. Ideally, you also want to start making money from your business before you quit your job. In addition to boosting your confidence in your ability to make it, you’ll also grow your nest egg.

3. Do you have a solid structure in place to help you create your business?

Without preparation and proper planning, quitting your job can put you in a conundrum: A vast amount of free time you don’t know how to use.

In the famous words of Lucille Ball, “If you want something done, ask a busy person to do it.” Surprisingly, it’s often easier to take on extra work when we’re already busy, yet harder to stay productive when we have too much time on our hands.

This reminds me of a few years ago when I was working 3 to 4 part-time jobs but found myself more productive than when I wasn’t working.

So, before you quit your job, it’s crucial to create some kind of structure to keep you productive. Here’s what I mean by structure:

  • An accountability system
  • A schedule with clear short-term and long-term goals
  • A set of rules to follow every day

An accountability system

After you quit your job, who will be there to call you out if you wind up watching cat videos instead of working on your business?

Accountability is extremely important. I suspect that one of the major reasons most people end up working for someone else is because of the accountability it provides. The majority of people just don’t have enough self-discipline to work for themselves.

The truth is, the freedom you’ll gain from quitting your job is useless without structure. When I left my job a few weeks ago, I realized how much I’d fought to create freedom in my life. Now that I’ve quit my job, I’m fighting to protect it.

Technically, I could take a month off and party every day. Doing that isn’t particularly important to me, but knowing that I can is. It’s having the option. That’s what freedom means to me.

Of course, this freedom won’t last unless I have the self-discipline to get up every morning and get the job done. To do that, I need to have a transparent system in place that holds me accountable.

There are several ways you can create accountability in your life. Let’s take a look at 4 of the best ways you can do it.

  1. Hiring a coach. Having a coach to support you can be very effective. It might be expensive, but the price you pay gives you skin in the game. You don’t want to waste your money, and that compels you to take consistent action towards building your business.
  2. Finding a mentor. Having a mentor can work wonders. You’ll benefit from their expertise, and they can hold you accountable for your actions.
  3. Joining a support group. Being part of group of people who have similar goals can be a great way to stay accountable and remain motivated. There will undoubtedly be someone with more experience who can provide valuable advice. You can also share your goals within the group, which is particularly beneficial for those who have a lot of naysayers in their lives. Of course, you’ll have to be an active member to reap the benefits of the group. This group can interact online or in-person, it all depends on what’s best for you.
  4. Having an accountability partner. Whatever you do, I highly recommend having someone you can contact regularly to share your progress. You could talk over Skype once a week to discuss where you’re at and what your goals are for the following week. You can also send each other a list of written goals on a consistent basis.

I myself am part of a personal development group as well as an author’s group on Facebook. I also send my schedule to my editor with specific deadlines for my articles and books, which helps me stay accountable.

What about you? How can you create more accountability in your life?

A schedule with clear short-term and long-term goals

Do you have a schedule you can follow once you quit your job? Do you know what you’ll do the day after you leave it?

To properly handle the sudden abundance of time you’ll experience, you need a preplanned schedule to keep you from slacking off. What are the main tasks that you need to work on? In what order will you work on them?

For instance, I know that I have to finish writing my books and articles by certain deadlines. While I don’t have my schedule all figured out, I do have specific projects scheduled.

I also set weekly goals, which generally include 2 or 3 big tasks that I want to have done by end of the week.

Additionally, I write down my goals on a piece of paper each morning. Typically, there are 2 or 3 main goals that I know I must achieve, along with a few other goals that I do my best to cross off my list.

I like to keep my list of daily goals on my desk so I can take off items as I move through the day. I usually focus on content creation (such as writing books and shooting videos) in the morning and save the afternoon for things like marketing and replying to emails.

If you need help setting goals, I encourage you to check out my goal-setting book here. It’s a comprehensive guide on how to effectively set goals.

A set of rules to follow each day

You won’t have a boss after you quit your job, but you’d better act as if you do. Establishing certain rules that you follow every day is a great way to stay consistent and create that clear structure you need.

Personally, I have a daily morning ritual that helps me maintain consistency. It includes powerful habits I need to start the day on a positive note and remain productive. These habits include things like meditation, gratitude exercises, stretching, affirmations, and goal-setting.

If you want to create a morning ritual, too, you can check my new book Wake Up Call – How to Take Control of Your Morning and Transform Your Life. It shows you step-by-step how to create a morning ritual.

4. Do you have enough savings?

Building a business takes time and money, and winding up back at your job in 6 months due to lack of funds is the last thing you want. Making sure you have adequate savings will prevent you from panicking after you leave your job.

The ideal situation would be having both savings and income from your business before pursuing it fulltime. You want to be in a situation where you can focus on your business for the next few years without worrying about money (or, worse yet, running out of it). You may even want to move somewhere with a lower cost of living or drastically reduce your expenses.

A common rule of thumb suggests maintaining 6 months of living expenses in your savings account at all times. This is especially beneficial if you’re leaving your job.

Lastly, you might also want to consider holding a part-time job if necessary. That could be particularly useful if you struggle with making effective use of your newfound free time. Aside from decreasing your money worries, you could become even more productive.

In conclusion

How well did you score on these four questions?

If you can answer all of these questions with an emphatic “YES”, you’ll be significantly more likely to create a fruitful business. If not, consider making the necessary adjustments to ensure your successful transition from employee to self-employed.

In closing, I’d like to wish you all the best with your business. I’d also love to know what kind of business you want to create in the future? Let me know below in the comments section 🙂

Wait! Before you leave don’t forget to SIGN UP to get your FREE copy of my ebook “Find What You Love”.

Comments 2

  • Hey mate, I usually totally agree with your view points. On this one, however, I see things differently. When I first started my online business, I didn’t have any self-discipline, I knew nothing about patience or perseverance, and I didn’t have a structure in place. Frankly, I had no idea what I was getting into.

    Here’s what happened: I developed all these things along the way. I grew my self-discipline, I became more patient, I was forced to persevere, and I created systems and strucutre.

    Important caveat, though. I was financially secure because I was still living at my parents’ place. So yeah, maybe the questions aren’t that bad after all 😉

    • Hello Nils. Yes, I also developed a lot of perseverance and self-discipline along the way. I’m still working on that these days! The point I was trying to make is that it’s better to test the water first. We all have some time to work on our side business in addition to our full-time job. If we can’t make that time, it means we aren’t really committed and that’s a red flag. However, of course, a lot of lessons will be learnt after we jumped 😉

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