50 Lessons I Learned After Quitting My $100,000+ Career

Michael Leonard


Nearly four years ago I left my safe, secure, 9–5 corporate job at Yelp.com.

At the time, I was earning over $100,000 as a national client partner in my late 20s. It took me six years to climb the corporate ladder and reach my dream position.

But by the time I reached the top sales position in the organization, I was checked out. It wasn’t the company either, it was working on someone else’s dream instead of my own.

I found that more money didn’t mean more fulfillment. I knew I had to do my own thing, so I could control my destiny.

So I saved up money and quit my six-figure job after making $200 from my blog in 2017. I’d love to tell you it’s been an easy ride but it would be a huge lie.

Needless to say, I just kept moving forward… inch by inch. After a lot of failing online ventures, I eventually found success as a freelance writer. That’s led to building an online brand, developing my skills, and never having to go back to a cubicle.

Being a digital entrepreneur means working on stuff you love, creating your schedule, and going all in your dreams. If you’ve ever thought of going out and building an online business, now is the time to get started.

50 Digital Entrepreneur Lessons

Here’s 50 lessons I’ve learned from my millennial life crisis to help you speed up success.

  1. Do what you love: There’s a niche for everything (literally everything) so make sure you love what you’re doing on a daily basis. If I can get paid to write about golf, I’m convinced you can make money in anything.
  2. Create multiple income streams: Having a job scares me because you only have one income stream. But as an online entrepreneur you can diversify your income streams (and I highly recommend it). For some ideas, check out a breakdown of my 11 income streams.
  3. Realize you have to change: You can’t be the same person as you were in the 9–5 world if you want to build your own business. I’ve found that your business is a reflection of you — personal growth goes hand in hand with growing your business. The more you evolve, the more money your business will generate.
  4. Expect friends to leave your life: Most people won’t get what you’re doing — even if you’re psyched about it. Make sure that you know who your real friends are and expect people to fade away if you don’t see them every day like you did at work.
  5. Learning is essential: I’ve learned more in three years than I would have in 30 years in a 9–5. To find success, keep consuming new content in your niche and about digital marketing to grow quickly.
  6. Avoid shiny object syndrome: The first two years I struggled because I was always going after the shiny new business (like e-commerce, YouTube fame, etc.). Instead, pick one thing and go all in to make the most progress.
  7. Use contracts in your business: That way you’ll protect yourself and your business when working with clients.
  8. Understand you can make money online in a lot of different ways: You’re the boss so you decided how you want to generate revenue with your business. But there’s no shortage of ways including — affiliate marketing, online courses, writing, online coaching, drop shipping, membership sites, ad revenue, etc.
  9. Get clear about what you want: Clarity is power. Spend time to figure out what you want (in explicit detail) so you can unleash the power of your mind to make it happen. This will also make it easy to say no to other projects and focus on what you want.
  10. Start side hustling before you quit: Prove your idea works before your quit your job. I did the exact opposite and it made the first year of freelancing a living nightmare.
  11. Minimize distractions: Working at home is hard because you can get lazy and not do anything productive if you don’t want to. Learn how to get in the zone by turning off your phone and getting into a flow state. This is vital to getting more done in less time and moving your business forward.
  12. Take time off: Sometimes the rest is the work. You’ll never get great ideas to move your business forward when you’re burnt out, exhausted, and overworked. Schedule off-time and commit to unplugging and recharging.
  13. Get a home office or co-working space: This will help have a defined work area and ensure you can separate work from life.
  14. Know your personality: Working at home is a lot easier if you’re naturally introverted. But if you’re an extrovert (or ambivert), make sure you get around people to recharge your energy levels. Knowing yourself and your personality will help you understand the right environment you need to thrive in.
  15. Money isn’t more important than mental health: Earning $20,050 in one month made me sacrifice my sanity and mental health. But let me tell you, it’s not worth it. Protect your mental health like your life and business depend on it (because they do).
  16. Expect family to doubt you: Your parents and family want you safe — entrepreneurship is anything but that. Just remember they love you and want the best, it’s nothing personal. Make them see what you’re doing by staying consistent and getting results.
  17. Save money before you quit: I saved up 12 months of living expenses before I quit, and can say it was the best thing I did. Cash is oxygen in your business and even though online businesses are a lot cheaper than brick and mortar, they still aren’t free.
  18. Invest in yourself: I’ve spent over $30,000 on online courses and coaching — and it’s been more than worth it. Speed up your learning curve in anything by learning from someone who already did what you want to do.
  19. Keep costs low: Saving money before you quit is key but keeping costs low is important as well. The more overhead you have, the more pressure you put on yourself to succeed early on. Building a business takes time so minimize overhead to not rush the process.
  20. Go to events and seminars: I’ve attended 20 or more events in three years and will say it’s a game-changer. Attending these events will help you get around quality people, help you get motivated, and create meaningful relationships with like-minded people.
  21. Network with fellow entrepreneurs: Find a local group (or at least a Facebook group) to connect with other people doing what you’re doing.
  22. Start an LLC: This will make it easier come tax time and keep you protected financially as well.
  23. Buy big purchases first: Getting approved for anything is harder when you’re self-employed, especially in the first few years when you’re trying to figure it out. So buy the big stuff (car, house, etc.) before you quit and still have that trusted 9–5 W-2.
  24. Understand that business income isn’t like a 9–5: If you want to make $100,000/year net income, then you’ll probably need to earn 1.5 to 2X in your business. You can’t forget to factor in extra taxes, business expenses, health insurance, etc. Luckily, writing doesn’t have a ton of overhead and can scale quickly.
  25. Forgive yourself often: You’re going to make a lot of mistakes when you work for yourself. Learn from your mistakes, remind yourself that you’re doing your best, and keep moving forward.
  26. Start practicing self-care: Entrepreneurship is stressful. Learn breathing techniques, yoga, meditation, and/or self-hypnosis to breathe and not get overwhelmed. This will help you stay level-headed when things go bad (and trust me they will at times).
  27. Upgrade your mind: Without the mindset of a champion, it’s easy to give up and go back to a 9–5. Study the mind and take care of your health (mental + physical) to develop a world-class mindset and not give up when things get tough.
  28. Keep your partner in the loop: Starting a business is like having a child, it will take a lot of your time and energy. It’ll mean long nights and early mornings which can mean less time with your partner. So make sure to let them know what you’re working on, how you’re progressing, and keep them in the loop. As always, communication is key, especially at the beginning of your entrepreneurial journey
  29. Don’t get complacent: Keep setting goals and never settle. If you can make $100 online, then you can make $1,000, then $10,000, then $100,000. But you have to keep pushing yourself so that you don’t plateau. When you hit a goal, celebrate it and set a new goal for yourself. Don’t let complacency creep into your business (or life)!
  30. Learn to love failure: The most successful entrepreneurs failed the most and the fastest. Once you reframe failure as learning opportunities, you give yourself permission to fail — which will make you successful.
  31. Hire a tax person: Business taxes are confusing! Don’t waste your time trying to learn them, just hire a professional for a few hundred bucks. Trust me, it’ll be the best money you’ve ever spent in your business.
  32. Use Gusto: Once you start making consistent income, sign up for Gusto so you pay yourself every two weeks. This will help for future loans and help you create budgets.
  33. Stay in a 9–5 if you want a safe and secure paycheck: There are no guarantees that you’ll make it. Entrepreneurship brings a lot of uncertainty — it isn’t for everyone. But when you make it work, there is no better feeling in the world.
  34. Have compelling reasons why you’re doing this: It’s going to get tough and you’re going to want to quit… unless you have compelling reasons why you’re doing this. Get clear about them and remind yourself of them constantly.
  35. Get a mentor or coach: While I love investing in online courses, getting a mentor will help you speed up success drastically. It’s nice to have 1:1 access to someone to get past any issues and have someone holding you accountable.
  36. Enjoy feeling scared: Growth only happens when you get out of your comfort zone. Cherish those “scary” moments and pursue them aggressively because they are pretty rare in a mundane 9–5 job.
  37. Buy a stand-up desk: Starting a business isn’t the 4-hour workweek (at least in the beginning). Since you’ll be behind your computer a lot, a stand-up desk can really help your posture and energy levels.
  38. Use social media: Think of social media as “business media” to grow your business, not waste your time. Be strategic with every moment you spend so you don’t get addicted to your phone (and not spend time on your business).
  39. Set an end time: Working at home makes it really hard to turn off sometimes. So make sure you have an end time so you can wind down and still enjoy your life. Just like you have a start time, you should also have an end time.
  40. Hire a VA: As my mentor once told me, “The reason you can’t hire a VA is because you haven’t hired a VA.” Trust me, even hiring someone 5–10 hours per week can help you with the small tasks and conserve your energy for the big ones!
  41. Document your journey: Whether it’s writing on Medium, starting a blog, YouTube channel, a business Instagram, or a podcast, keep people in the loop. This will help you build an audience and it’s fun to see how much you evolve over time.
  42. Review your goals often: Keep reminding yourself what you want your business to look like. Imagine, visualize, and affirm that it will happen (even if it feels like you’re far away). Doing this will reprogram your mind for success and make them more likely to come true.
  43. Create a motivational playlist: Whether it’s on Spotify or YouTube, have a go-to playlist when you need to get motivated! Since no one is going to look over your shoulder like a traditional job, it’s up to you to get inspired and take action.
  44. Focus on what you want: Don’t spend any of your time worrying about what you don’t want to happen. Instead, focus all of your efforts on creating the future you desire. Plus, getting anxious about the future won’t help anything but it will ruin your current mood and productivity levels.
  45. Believe in yourself: Humans can do extraordinary things. If you have a dream to do something great, you can do it… but only if you believe in your potential. No one can do this for you, this is an internal game
  46. Create a 3-year vision: I’ve found three years is the perfect amount of time for a vision (not goals). It’s long enough to give you time to make it happen but short enough to still have a motivating deadline.
  47. Journal your wins constantly: Every day or week, write down your wins in a journal specific to wins only. That way when you have a bad day, you can open it up and remember how much you’ve accomplished.
  48. Celebrate your wins: Once you have your journal, celebrate all of your wins — big or small! This will help you get in the habit of winning and breed even more wins in the future.
  49. Join a mastermind: Once you’re making some consistent income, it’s crucial to get around people earning more than you. Joining James Wedmore’s 12-month group coaching mastermind has been the best money I’ve ever spent in my business. There is power in proximity so get around more successful people, and they’ll wear off on you.
  50. Have fun: As Steve Jobs said, “I have looked in the mirror every morning and asked myself: ‘If today were the last day of my life, would I want to do what I am about to do today?’ And whenever the answer has been ‘No’, for too many days in a row, I know I need to change something.” Never forget that life is short, so spend time doing what you love.

Final Thoughts

Truthfully, I can’t believe it’s been three years since I left the corporate world. Some parts of me feel like it was yesterday, while other parts feel like it’s been a decade.

I will say working for yourself is a beautiful self-discovery adventure, but just know it’s not going to be easy. It’ll test you more than any job ever will, but if you keep going, amazing things will happen.

Use these 50 tips to start your passion business and make your dream of entrepreneurship come to life.

Life’s too short to work at a job you hate.

*Photo provided by Wavebreakmedia on Deposit Photos

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My name is Michael Leonard and I am the creator of Inspire Your Success. I'm on a mission to help readers build online writing businesses and quit their jobs to live a life of freedom!

Scottsdale, AZ

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