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10 Questions to Ask Yourself Before Quitting Your Job

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Suits TV show Office quit Job

Admit it? You’ve wondered if you should take the plunge.

You detest working for an unappreciative company every day, you’re un-challenged, and you have no chance of getting promoted, no matter how much you bust your butt.

Maybe it’s time to face the music?

And accept the fact that you’re seriously unhappy in your job, and nothing will change that.

So you can’t help wondering?

Why not do what many others have done before you? Pursue your dream, follow your passion, become an entrepreneur, and be happy?

If the above describes you, then, yes, you should seriously consider that option.

The following 10 questions will help you to get started

 

1. Do I really want to work for myself?

Is this business or entrepreneurship in general really something you dream about?

Or are you just trying to escape something you don’t like, such as your current boss, your daily commute, or your industry?

If you’re serious about entrepreneurship and following your passion, that’s great. But if you’re just upset with your boss, that is not a good enough reason to quit your job and seek entrepreneurship.

 

2. Am I willing to lose my significant other and alienate my friends and family?

If your partner, friends, and family are not fully behind your pursuit of entrepreneurship, it will strain these relationships, maybe even end them all together.

If you aren’t willing to go through these changes in your relationships, quitting your job to pursue your dreams might not be for you. If you are, you may find that the new relationships you develop are what you had been yearning for all along.

 

3. Will I be able to support myself for a year as a Start Up?

The least risky way into entrepreneurship is what Derek Sivers (Founder of CD Baby) calls The Tarzan Technique.

Stay gainfully employed, start your own business as a side hustle, and quit your current job when you can monetize your business.

Like Tarzan swings through the jungle, don’t let go of the old support until you have a firm grip on the new one, and then keep swinging.

 

4. Am I willing to work 80 hours a week?

Like Lori Greiner said,

“Entrepreneurs are willing to work 80 hours a week to avoid working 40 hours a week.”

Starting your own business means you have to do whatever it takes, and that is not always fun.

You will face long working hours and sleepless nights, but all that you sacrifice now is only to have more of it in the future.

If this is too much of a detriment for you, getting into entrepreneurship might not be for you, so keep your job.

 

5. Can I live with failure?

Failure is part of the journey to success; just ask any wildly successful person. They have all failed more than once? Nothing to be afraid of.

You might fail, but it’s a chance to learn and just another stepping-stone to your success.

The only real failure is doing nothing simply because you’re too afraid to make a mistake.

After all, what is the worst that can happen? That you may end up exactly where you are right now.
If you cannot live with failure, entrepreneurship is not for you. If you think you can, great.

 

quitting a job quote
 

6. Can job security totally ruin my life?

Many people see staying gainfully employed as a safer choice.

But it’s probably fair to say that if you spend most of your waking hours living in misery in exchange for job security, doing so would ruin your life.

If questionable job security means more to you than pursuing your dream, starting your own business is most likely not a good idea.

 

7. How disciplined am I?

If you want to be your own boss, you must be able to motivate yourself.

This can be difficult, especially at the beginning when customer demands aren’t yet forcing you to be productive.

If you know you lack discipline, quitting your job to pursue your dreams might not be right for you.

 

8. Does my passion fulfill a market need?

Breaking free, chasing your dreams, and following your passion can be a fantastic thing to do, but if your passion has to pay your bills, you need to look at it as a business too? Or you will be broke.

Remember, clients spend money on services that fulfill their own desires. You can only be happy and financially successful by following your passion, one that fulfills a need the market has.

If there is no market for what you’re passionate about, you should not quit your job as it will lead to financial disaster.

 

George Carlin Quote Get Fired from Your Job
9 Powerful Quotes That’ll Inspire You to Be Your Own Boss
 

9. What do I suck at?

There must be some stuff you?re not so good at. So what is it?
Before you jump into entrepreneurship, you must have the skills to make your business a success.

Close your skill gap, and brush up on social media marketing and the latest trends.

Staying current is critical to your success. If you are completely unaware of what you suck at, you are not ready to start a business.

In a twisted way, knowing what is holding you back is your best recipe for success, in almost everything.

 

10. Are you willing to put your ego aside for your business?

As a young entrepreneur, you must be able to understand and listen to your customers, process feedback, and improve what’s needed, even if it’s very personal.

And despite all the tippy-toe dances, you still have to be the boss.

Make sure your EGO doesn’t get in the way.

It will probably tell you that you know it all (remember #9), kill your objectivity, and give you tunnel vision.

If you can’t control your EGO, you’re not ready for entrepreneurship yet.

 

What’s the Point?

Do you think you’re ready to quit your job to pursue your dreams, follow your passion, and become a successful entrepreneur?

I’d love to tell you that taking the plunge into entrepreneurship is a breeze.

I’d love to tell you that it’s going to be easy.

I’d love to tell you that you can do it between lunch and dinner.

But you already know that I won’t do that, right?

You have heard dishonest, “How To” advice many times before, but we won’t lie to each other, will we?

Getting out there and creating a future is a big thing, and it’s hard work. But if you answered “yes” to the questions above, it’ll all be worth it in the end.

If you’re ready to take the plunge, don’t procrastinate any longer.

Start now; a life you love awaits you. So hurry up; what are you waiting for?

Wilfried Lehmkuhler is passionate about helping people achieve their dreams; create financial Freedom and a Life they love by applying proven success strategies. Wilfried is a blogger, speaker, consultant, and accomplished author who has worked with professional athletes and businesses in Europe and North America. You can find him at FinancialFreedomAndALifeYouLove.com or @WLehmkuhler

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Life

How Learning the Skill of Hope Can Change Everything

Hope isn’t wishful thinking. It’s a state of being and a skill that has profound evidence of helping people achieve success in life

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Hope as a skill
Image Credit: Midjourney

Hope isn’t wishful thinking. It’s a state of being and a skill that has profound evidence of helping people achieve success in life.

Wishful thinking, on the other hand, is like having dreams in the sky without a ladder to climb, having a destination without a map, or trying to operate a jet-engine airplane without instructions. It sounds nice but is impossible to realize. You don’t have what you need to make it happen!

What Real Hope Is

Real hope is actionable, practical, and realistic. Better yet, it’s feasible and can be learned.

One popular approach is Hope Theory. This concept is used by colleges to study how hope impacts students’ academic performance. Researchers found that students with high levels of hope achieve better grades and are more likely to graduate compared to those with less hope.

Hope can be broken down into two components:

  1. Pathways – The “how to” of hope. This is where people think of and establish plans for achieving their goals.
  2. Agency – The “I can” of hope. This is the belief that the person can accomplish their goals.

Does Hope Really Work?

According to Webster’s Dictionary, hope as a noun is defined as: “desire accompanied by expectation of or belief in fulfillment.”

As humans, we are wired to crave fulfillment. We have the ability to envision it and, through hope, make it a reality.

My Experience with Hope

For 13 years, I was a hopeless human. During my time working at a luxury hotel as a front desk agent earning $11.42 per hour, I felt the sting of hopelessness the most.

The regret of feeling my time was being stolen from me lingered every time I clocked in. Eventually, I decided to do something about it.

I gave myself permission to hope for something better. I began establishing pathways to success and regained agency by learning from self-help books and seeking mentorship.

Because I took action toward something I desired, I now feel more hope and joy than I ever felt hopelessness. Hope changed me.

Hope Actually Improves Your Life

Wishful thinking doesn’t work, and false hope is equally ineffective. Real hope, however, is directly tied to success in all areas of life.

Studies show that hopeful people tend to:

  • Demonstrate better problem-solving skills
  • Cultivate healthier relationships
  • Maintain stronger motivation to achieve goals
  • Exhibit better work ethic
  • Have a positive outlook on life

These benefits can impact work life, family life, habit-building, mental health, physical health, and spiritual practice. Imagine how much better your life could be by applying real hope to all these areas.

How to Develop the Skill to Hope

As acclaimed French writer Jean Giono wrote in The Man Who Planted Trees:
“There are also times in life when a person has to rush off in pursuit of hopefulness.”

If you are at one of those times, here are ways to develop the skill to hope:

1. Dream Again

To cultivate hope, you need to believe in its possibility. Start by:

  • Reflecting on what you’re passionate about, your values, and what you want to achieve.
  • Writing your dreams down, sharing them with someone encouraging, or saying them out loud.
  • Creating a vision board to make your dreams feel more tangible.

Dreams are the foundation of hope—they give you something meaningful to aspire toward.

2. Create an Environment of Hope

  • Set Goals: Write down your goals and create a plan to achieve them.
  • Visualize Success: Use inspirational quotes, photos, or tools like dumbbells or canvases to remind yourself of your goals.
  • Build a Resource Library: Collect books, eBooks, or audiobooks about hope and success to inspire you.

An environment that fosters hope will keep you motivated, resilient, and focused.

3. Face the Challenges

Don’t avoid challenges—overcoming them builds confidence. Participating in challenging activities, like strategic games, can enhance your problem-solving skills and reinforce hope.

4. Commit to Wisdom

Seek wisdom from those who have achieved what you aspire to. Whether through books, blogs, or social media platforms, learn from their journeys. Wisdom provides the foundation for real, actionable hope.

5. Take Note of Small Wins

Reflecting on past victories can fuel your hope for the future. Ask yourself:

  • What challenges have I already overcome?
  • How did I feel when I succeeded?

By remembering those feelings of happiness, relief, or satisfaction, your brain will naturally adopt a more hopeful mindset.

Conclusion

Hope is more than wishful thinking—it’s a powerful skill that can transform your life. By dreaming again, creating a hopeful environment, facing challenges, seeking wisdom, and celebrating small wins, you can develop the real hope necessary for success in all aspects of life.

Let hope guide you toward a brighter, more fulfilling future.

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Life

The 5 Stages of a Quarter-Life Crisis & What You Can Do

A quarter-life crisis isn’t a sign you’ve lost your way; it’s a sign you’re fighting for a life that’s truly yours.

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what is a quarter life crisis
Image Credit: Midjourney

The quarter-life crisis is a well-defined set of stages—Trapped, Checking Out, Separation, Exploration, Rebuilding—one goes through in breaking free from feelings of meaninglessness, lack of fulfillment, and misalignment with purpose. I detail the stages and interweave my story below. (more…)

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Life

Here’s The Thing About Learning, Unlearning, and Relearning

Stop hoarding and start sharing your knowledge and wealth for the benefit of humankind

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sharing your knowledge
Image Credit: Midjourney

Few people have the habit of hoarding their wealth without spending.  However, it limits their motivation as they tend to get into their comfort zones.  When people start spending money, then there will be depletion in their coffers. (more…)

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Life

3 Steps That’ll Help You Take Back Control of Your Life Immediately

The key to finding “enough” is recognizing that the root of the problem is a question of self-esteem and deservedness

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How to build self worth
Image Credit: Midjourney

“It’s never enough.” (more…)

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