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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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Entrepreneurs

The Brutal Truth About Entrepreneurship with ADHD (And Why Most Advice Is Making It Worse)

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Image Credit: Joel Brown - Addicted2success

You’re not lazy. You’re not undisciplined… and you’re definitely not broken.

You’re an entrepreneur with ADHD, and right now you’re probably sitting on 19 unfinished projects, 47 open tabs, and a brain that feels like it’s running on 12 different radio stations at once.

You’ve read the books. You’ve tried the planners, the Pomodoro timers, the accountability groups. You’ve even hired coaches who promised to “fix” your focus. Yet here you are — brilliant ideas, massive potential, and a business that still feels like it’s one step away from collapsing under the weight of your own mind.

Here’s what almost nobody in the entrepreneurial space will admit:

The real struggle isn’t your ADHD. It’s that you’ve been trying to run a neurodivergent brain inside a neurotypical business model — and then beating yourself up when it doesn’t work.

Most advice for entrepreneurs was written by people whose brains work differently. They preach consistency, routines, long-term planning, and steady execution like those things are universal truths. For the ADHD entrepreneur, those “truths” feel like trying to swim upstream in cement. You can force it for a while (and you have), but eventually your brain rebels, the burnout hits, and you’re left feeling like a failure who just needs to “try harder.”

That cycle is quietly destroying more talented founders than cash flow problems or bad hires ever could.

The deeper layer most people never reach is this: your ADHD isn’t a bug in the system. It’s a different operating system entirely. And when you stop trying to install Windows on a Mac and start building everything around macOS, the game changes completely.

The Hidden Addiction That Keeps ADHD Entrepreneurs Stuck

You already know the surface symptoms — time blindness, rejection sensitivity, starting strong and fading fast, shiny object syndrome.

But the real trap is more insidious.

It’s the addiction to chaos and novelty.

Your brain is wired for dopamine. New ideas, big visions, last-minute sprints, high-stakes pressure — these things light you up like nothing else. The boring, repetitive, systems-building work that actually scales a business? It feels like torture.

So unconsciously, you keep your business in a state of controlled chaos. You say yes to too many things. You chase the next exciting opportunity. You avoid building the boring infrastructure because “I work better under pressure anyway.”

And every time the pressure gets too high, you crash, swear you’ll get organized next quarter, and repeat the cycle.

Meanwhile, the neurotypical advice keeps telling you to “just build better habits.” As if your brain is a poorly trained dog that needs more discipline instead of a high-performance race car that needs the right fuel and track.

This isn’t a character flaw. It’s neurology.

And until you stop treating your wiring as something to overcome and start treating it as your greatest strategic advantage, you’ll stay stuck in the same exhausting loop.

The Identity Shift That Changes Everything

The entrepreneurs with ADHD who finally break through don’t “fix” their brains.

They redesign their entire business to work with their brains.

They stop trying to become the consistent, routine-loving founder the gurus talk about. Instead, they become the architect of a system that leverages their natural strengths — hyperfocus, pattern recognition, creative problem-solving, relentless drive under pressure — while outsourcing or automating everything that drains them.

This is the layer most ADHD entrepreneurs never reach because it requires something terrifying: accepting that you are never going to be “normal” at entrepreneurship… and that’s exactly why you can win bigger than most.

Your ability to see connections others miss. Your tolerance for uncertainty. Your capacity to go all-in when something lights you up. These aren’t liabilities. They’re unfair advantages in a world that rewards speed, creativity, and bold moves.

The shift is simple but brutal:

Stop trying to manage your ADHD. Start designing your business around it.

How to Actually Build a Business That Works With Your Brain

  1. Stop fighting your energy cycles — weaponize them. Most ADHD entrepreneurs try to force 8-hour focused days. That’s insane. Instead, track when your brain actually works best (for many it’s 10pm-2am or random 4-hour hyperfocus bursts). Build your schedule around those windows. Protect them like gold. Do the deep, high-leverage work then. Use the low-energy periods for admin, calls, or recovery.
  2. Build “chaos containers,” not rigid systems. Traditional project management tools feel like cages. Create loose but effective structures that give your brain freedom. Use tools like Notion with massive flexibility, or body-doubling (working alongside someone virtually), or even hiring a “chaos wrangler” — an assistant who thrives on turning your scattered ideas into executable plans.
  3. Turn your rejection sensitivity into rocket fuel. That intense fear of letting people down or looking stupid? Channel it into creating ridiculously high standards for your customer experience or product quality. Use it as fuel instead of letting it paralyze you.
  4. Outsource the parts that make you want to die. The execution, follow-through, and maintenance phases are where most ADHD entrepreneurs lose. Hire or partner with people who love the details. Your job is vision, strategy, and big swings. Let someone else own the spreadsheets.
  5. Create external pressure on your own terms. Deadlines and public commitments work wonders for the ADHD brain. Use them strategically — announce launches, create beta groups, or work with coaches who understand neurodivergence instead of fighting it.

The entrepreneurs with ADHD who are quietly crushing it right now aren’t the ones who finally became “disciplined.” They’re the ones who stopped apologizing for how their brain works and started building empires that are specifically engineered for it.

They have teams that handle the boring stuff. They have systems that flex with their energy instead of fighting it. They’ve turned their “flaws” into the exact reasons their businesses stand out.

Your ADHD brain is not the enemy. The enemy was trying to play the game by rules that were never designed for you.

The moment you accept that and start designing everything… your calendar, your team, your offers, your processes — around how you actually operate, the struggle doesn’t disappear… but it becomes manageable, even exhilarating.

You were never meant to fit the mold. You were meant to break it and build something better.

The world doesn’t need another cookie-cutter entrepreneur. It needs the chaotic, brilliant, all-in, slightly unhinged visionaries who can only operate at full power when the game is built for them.

That’s you.

Stop trying to fix yourself. Start building the business that was always meant to be run by a mind like yours.

Your next breakthrough isn’t going to come from working harder or being more consistent. It’s going to come from finally giving yourself permission to work differently.

And when you do that? Watch what happens.

The same brain that once felt like a curse becomes the exact reason your business becomes unstoppable.

You’ve got this. Not despite the ADHD. Because of it.

If you want to learn more from me or send me a personal message I’ll respond to you on Instagram at https://instagram.com/iamjoelbrown speak soon!

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Health & Fitness

The Health Planning Habits That Support Long-Term Success

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Image Credit: Joel Brown - Addicted2success

Most people think about health planning only when something forces them to.

A medical bill arrives unexpectedly. An insurance issue appears during treatment. A diagnosis changes how future care needs are viewed. Suddenly health planning becomes urgent instead of preventative.

The problem is that long-term health stability is usually shaped by smaller habits built quietly over time, not just by major decisions during emergencies.

That includes physical health habits, of course, but it also includes how people approach insurance coverage, preventative care, financial preparation, and long-term healthcare planning before problems become immediate.

The families who navigate healthcare stress most effectively are often not the ones avoiding every issue entirely. More often, they’re the ones who built systems early enough to make difficult situations feel more manageable later.

Consistency Matters More Than Perfection

A lot of health advice still revolves around extreme change.

Perfect diets. Aggressive routines. Complete lifestyle overhauls.

In reality, most long-term health success comes from consistency people can realistically maintain for years instead of months. Small preventative habits tend to matter more than dramatic short-term efforts that collapse under pressure.

That principle applies financially too.

People often spend more time researching investment strategies than understanding their healthcare coverage or preparing for future medical costs. But healthcare instability can disrupt long-term financial plans surprisingly quickly when households are unprepared for how expensive even routine care can become over time.

The practical side of health planning is becoming harder to separate from overall financial planning now than it used to be.

Preventative Planning Reduces More Stress Than People Realize

One overlooked benefit of health planning is emotional stability.

People who understand their coverage, maintain preventative care routines, and think ahead about healthcare decisions often describe feeling less overwhelmed when unexpected situations happen. The goal is not eliminating uncertainty entirely. That’s unrealistic.

The goal is reducing how chaotic healthcare decisions feel under pressure.

That’s one reason broader conversations tied to healthcare and health insurance have expanded significantly over the last several years. Rising costs, changing coverage structures, and increasing healthcare complexity have made long-term planning more important for average households than many people expected.

Healthcare is no longer something most families can comfortably approach reactively forever.

People Underestimate How Quickly Healthcare Costs Compound

One reason health planning habits matter so much is that healthcare costs rarely arrive in one dramatic moment alone.

More often, they build gradually:

  • recurring prescriptions
  • specialist visits
  • ongoing treatment plans
  • insurance deductible increases
  • long-term care considerations
  • unexpected procedures layered on top of existing expenses

Families often absorb these costs incrementally until they realize how much financial pressure accumulated over time.

That gradual buildup is part of what makes proactive planning valuable. People who think ahead about coverage structures, emergency savings, provider networks, and preventative care tend to adapt more smoothly when healthcare needs eventually increase later in life.

The difficult part is that many households delay these conversations because they feel healthy right now.

Healthcare Decisions Have Become More Complicated

Another challenge is that healthcare systems themselves continue evolving quickly.

Insurance structures change. Telehealth expands. Employer-sponsored benefits shift. Prescription pricing fluctuates. Patients now carry more responsibility for understanding deductibles, provider networks, and out-of-pocket exposure than previous generations often did.

That complexity creates decision fatigue.

Even relatively organized households sometimes feel uncertain about whether they’re making good healthcare choices because the systems themselves are difficult to navigate confidently. A lot of current health insurance trends discussions reflect this larger issue, healthcare planning is becoming less about isolated medical events and more about long-term sustainability across entire households.

People want predictability, but healthcare systems increasingly feel harder to predict.

The Most Effective Health Habits Usually Feel Boring

One thing people rarely admit is that good long-term planning habits are often not particularly exciting.

Scheduling preventative appointments. Reviewing insurance annually. Building emergency savings slowly. Staying physically active consistently. Maintaining realistic routines instead of dramatic cycles of burnout and reset.

None of those habits feel dramatic at the moment.

But over long periods, they create stability that becomes incredibly valuable once life gets complicated. The people who navigate healthcare stress most effectively are often the ones who built ordinary systems early instead of waiting for perfect motivation later.

That applies financially and physically at the same time.

Why Long-Term Success Depends on Adaptability

Health planning is ultimately difficult because people’s lives keep changing.

Careers shift. Families grow. Aging parents require support. Medical needs evolve. Financial priorities change over decades in ways nobody predicts perfectly in advance.

That’s why the strongest long-term health planning habits are usually flexible rather than rigid.

The goal is not building a flawless plan that never changes. It’s creating enough structure, awareness, and preparation that future adjustments become manageable instead of overwhelming.

Most people cannot control every future health outcome. They can, however, build habits that make uncertainty easier to navigate when it eventually arrives.

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Life

Why Moving to a New City Can Change Your Mindset

Discover how moving to a new city boosts neuroplasticity, builds resilience, and reshapes your mindset

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How relocation changes your mindset

Relocation is always a challenge. Rebuilding and restarting your life requires you to step outside of your comfort zone. (more…)

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Change Your Mindset

The Hidden Reason You Can’t Stay Consistent

If motivation keeps failing you, the real issue isn’t discipline. It’s the identity shaping your habits and long-term success.

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Identity-based habits

Success often looks like a time-management problem. You buy a planner, set reminders, and hope that next week will be different. For a few days, it works. Then stress hits, motivation drops, and old patterns return. (more…)

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