“I decided to start my own business now instead of waiting to graduate.”
I shared this with an uninterested classmate when I started this blog sixteen years ago, all the way back in 2008. I’m not sure where the time went, but here we are, and I’m a 36-year-old writing about personal finance while getting to live the entrepreneur lifestyle (no, I’m not sitting at the beach as I type this).
One month into my blogging career, I sold my first text link for $20 and thought I had it made. Luckily, I didn’t let it get to my head, so I graduated from college still despite coming into this newfound wealth.
I wanted to share 16 lessons from 16 years of entrepreneurship that I had to learn the hard way to help you save money, time, and headaches (and possibly heartbreak).
When I was first mentioned in the New York Times or asked to appear on news segments, I couldn’t believe people were paying attention to my blog. There’s nothing like typing words into your laptop and not knowing where they will end up, only to find out that there are actual human beings on the other end applying what you’re saying. While these days it’s easier to get instant feedback for your work with social media, it’s still risky to publish your work. You don’t know if anyone will care and are worried about what people will say if they consume your stuff.
Here are 16 random lessons from 16 years of blogging and entrepreneurship…
Lesson #1: There’s never a perfect time to start.
You’ll never start anything if you wait for the right time to launch. You have to stop trying to convince yourself that you’ll start that project when you have more free time in the future because there likely won’t be a time in your life when you have the ideal conditions.
It took me too long to start when I waited until the end of 2008 to launch, but I have friends who still haven’t followed through after all of these years. I studied through the summer of 2007 to have the winter off from school to focus on a business venture (nothing in particular). I read articles and books on entrepreneurship from January until September of that year, waiting for the perfect moment to launch. By September, I realized that all I had accomplished was reading a bunch of books on being an entrepreneur. In case you’re wondering, reading books on entrepreneurship doesn’t make you an entrepreneur.
There are a million quotes about why you shouldn’t wait to start. I’ve learned from myself and every successful person I’ve interviewed for my podcast that they just started before everything was figured out.
Here’s the harsh reality about entrepreneurship: if you need motivation to start, maybe this isn’t for you.
There’s no perfect time to start because your life will never get easier. You don’t need another self-help book or a list of motivational quotes, either.
“For all of the most important things, the timing always sucks. Waiting for a good time to quit your job? The stars will never align and the traffic lights of life will never all be green at the same time. The universe doesn’t conspire against you, but it doesn’t go out of its way to line up the pins either. Conditions are never perfect. ‘Someday’ is a disease that will take your dreams to the grave with you. Pro and con lists are just as bad. If it’s important to you and you want to do it ‘eventually,’ just do it and correct course along the way.” — Timothy Ferriss, “The 4-Hour Workweek”
Lesson #2: The best way to learn anything is through on-the-job training.
“How did you figure this out?”
I’ve been asked this many times about learning different things, and the answer is always the same. I learned on the job through trial and error. Almost everything you want to learn about has been documented in excruciating detail, and you’re not alone in any journey. If you don’t believe me, look through Google, Instagram, YouTube, or TikTok. You’ll find a tutorial for anything that you’re ever stuck on (from language lessons to finding a viral hook for your 6 second reel).
I’ve applied this logic to other areas of my life where I had to teach myself:
- Getting into Airbnb management.
- Starting an Airbnb Experience.
- Learning new sports.
- Growing an Instagram page.
- Figuring out how to get Google’s readers to read your blog.
- Starting a podcast without any technical skills (subscribe to Do You Even Hustle).
- Editing videos for social media with zero editing skills.
- Going on a solo trip to a place where I don’t speak the language.
You can only figure things out by learning on the job because theories will never replace real-world experience.
Lesson #3: Your role models are also trying to figure it out.
It can be daunting to start when you look around; it feels like everyone else has it all figured out. The good news is that most people don’t actually have this figured out at all because they’re also just trying to do their best. Those who act like they have it all figured out, are usually fraids or highly delusional.
I’ve been lucky enough to become friends with people I initially looked up to, and I can confirm that most are trying to figure it out as they go.
This means you shouldn’t feel intimidated if you don’t have all the answers or are nervous about a project. You’re not the only one. Your role models are also winging it and doing their best to get to the next day.
Lesson #4: You have to invest in yourself and your business consistently.
A friend asked me what podcast tools they needed to get started. So, I shared a link to a mic and a hosting server that were non-negotiable. They complained about the price and never launched. Spending $100 upfront on those tools was all that they had to do to get started, but that was too much for them. While $100 may feel like a decent chunk of change, it’s not much when you consider that you want this project to become your primary source of income one day.
If you want to get results in any field, you have to invest in it to prove that you’re serious. Why would anyone invest in you if you’re not willing to invest in yourself?
How can you invest in yourself?
- Attend events. You want to learn from others and meet people in your field so that you can be part of the community.
- Read books. Everything you could want to do has been written about, so learn from those who are ahead of you.
- Invest in the best tools for your business. You want to ensure that you have the right tools to grow your business and you absolutely can’t be cheap here.
- Keep on learning new skills. As an entrepreneur, you’re going to want to continuously invest in learning new skills because entrepreneurship in itself isn’t one specific skill. You have to learn about sales, marketing, handling customers, dealing with staff, time management, and so on.
You’ve already heard about the importance of investing in yourself, so it’s time to take action. To learn how to get started, read the ultimate guide I put together on investing in yourself.
Lesson #5: You never know what idea will take off.
“Entrepreneurs struggle to differentiate between idea and execution. They think ideas are worth millions, when success is never about the idea but about the execution.” — MJ DeMarco, “The Millionaire Fastlane”
Since I started in this online world, I’ve seen some of the most absurd ideas take off. It feels like you can’t go online without hearing about some silly new concept that has become popular or some new viral sensation that has taken off.
Here’s the thing about ideas: you never know what will be a hit.
Hawk Tuah, right?
Keep testing your ideas because the market will tell you whether they are good. Don’t worry about finding out that an idea doesn’t work either because this gives you the feedback needed to try something else.
Lesson #6: You have to be around others who are on a similar path.
You can’t try to do this alone, and it would help if you also had people around you who could inspire you. This means that you’ll want to find other entrepreneurs to connect with so that you have friends to relate to.
How can you change this?
- Find a way to be around people doing what you want to do. There are Facebook groups, masterminds, meet-ups, and events where they gather. Go there.
- Avoid those who doubt you and what you’re doing. If you’re pursuing a project that excites you, and someone in your social circle doubts you, they’re a loser. Avoid them. There’s nothing wrong with feedback, but to get mocked isn’t acceptable.
- Pay for mentorship. You can speed up the process by paying for mentorship. In the perfect world, you would find someone willing to mentor you, but you’ll likely have to pay for it these days.
- Pay for access to people you want to be around. This may require you to spend money on coaching, joining a mastermind, or something similar.
Lesson #7: Working out and staying active is the ultimate productivity hack.
“Nothing has a greater effect on your ability to enjoy experiences—at any age—than your health. In fact, health is actually a lot more valuable than money, because no amount of money can ever make up for very poor health—whereas people in good health but with little money can still have many wonderful experiences.” — Bill Perkins, “Die With Zero”
As an entrepreneur, you don’t have co-workers most of the time, so you have to create your own social circle. You also have to do whatever you can to stay productive, which means you’ll want to ensure you have lots of energy. I personally stay active by lighting weights and attending jiujitsu classes during the day. Going to lift weights in the afternoon or dropping in for a grappling class helps me stay focused and energized throughout the day. You can’t skimp on your health because you want to show up as your best self as often as possible.
Lesson #8: Pivot instead of giving up.
There will be times when you feel like giving up. You see your friends moving up in their careers and progressing while you’re waiting for your big break. It’s easy to give up; truthfully, entrepreneurship isn’t for everyone. However, before you call it quits, you’ll want to try pivoting first.
The best part about pivoting is that you’re not starting off fresh again. You’re taking all of your experiences with you.
I’ve had to pivot many times in my career, which is how I became a freelance writer again.
Lesson #9: You can’t be jealous of anyone’s success.
The toughest thing to do is cheer for others when they’re winning when you feel like you can’t catch a break.
I’ve been in this position numerous times. I wish I could say that it’s easy. You just have to trust that your time will come. Someone else becoming successful doesn’t make you a failure, nor does it impact you.
Lesson #10: It takes a decade to be an overnight success.
In the age of going viral, you can feel like a failure when you don’t make it big in your first six months. The truth is that most people who go viral or feel like an overnight sensation have been at it for years.
I promise you that like 99% of entrepreneurs don’t become viral sensations.
It could take you a decade to become an overnight success.
Lesson #11: Don’t beg people to support you.
If the people in your life don’t support you, you can’t force them to do so. It’s frustrating when nobody believes in you, but begging them to help you won’t make it better. You have to try to find your audience and a group of peers so that you’re not constantly housing you social circle to support you.
Lesson #12: Focus on ONE thing.
“When you try to do two things at once, you either can’t or won’t do either well. If you think multitasking is an effective way to get more done, you’ve got it backward. It’s an effective way to get less done. ” – Gary Keller, “The ONE Thing”
This is one lesson that I struggle with applying to my own life. I always work on multiple projects and get distracted with random tasks. If you want to become successful in one thing, you have to accept that you’re not going to make it at everything. You have to zero in your focus on a major project so that you’re not trying to grow a YouTube channel on cooking while building up an Instagram page on travel and testing out some random affiliate marketing project.
Lesson #13: You shoud be experimenting in real life.
“The arrow doesn’t seek the target, the target draws the arrow. We must be aware of what we attract in life because it is no accident or coincidence.” — Matthew McConaughey, “Greenlights”
I’ll spare you the typical quotes on escaping your comfort zone. You can’t create compelling content if you don’t live a little. You won’t become interesting until you do exciting things worth sharing.
Lesson #14: You have to strike the right balance between getting paid today and getting a bigger payday in the future.
The one thing that most people don’t realize about entrepreneurship is that you have to put a ridiculous amount of effort and energy into projects that may not pay off. For example, you could spend months growing a software company or trying to build a course without turning a profit or even bringing any money in. The goal is to cash out large when you eventually get paid, but there are absolutely no guarantees.
This means that you may have to take on freelance work as you grow your business. Sometimes, you may even have to take a part-time job just to get by until your business takes off.
Lesson #15: Failure is part of the process.
“Failure is the information you need to get where you’re going.” — Rick Rubin, “The Creative Act.”
You’re going to fail as an entrepreneur. You’re going to fail often. Social media is filled with success stores because those who fail usually just end up going away.
While there are plenty of motivational quotes about the importance of failing, the reality is that it’s a terrible feeling. Nobody sets out to flop on their goals. You don’t want to be the person who DIDN’T make it because they never write headlines about those who came close.
However, when taking big chances and challenging yourself, you’re bound to experience setbacks. To use a sports analogy, you don’t always hit a home run, and you may even strike out every time you go up for a long time. You have to be able to handle many bad days in a row if you want to be an entrepreneur for a long time.
“Only failure of omission is real failure. Because if you don’t do something, you can’t learn from your experience. Every experience is a teacher, filled with enough lessons to carry you to the next level of your education in any field.
Again, the habit of constantly experimenting in all facets of your life will bring you enormous success. With each experiment you are either adding to your knowledge or you are succeeding and propelling forward in the hierarchy of that interest/passion/career.” — James Altucher, “Skip The Line”
Lesson #16: People are willing to help those who help themselves.
Most people are willing to help you out if you ask for it and are open to feedback. I’ve been extremely fortunate to get help along the way throughout my entire journey as an entrepreneur. You don’t have to feel like you’re alone because there’s no such thing as “self-made.” We all rely on others to help us out. The sooner that you embrace this, the better off that you’ll be.
Stop trying to do everything alone and ask for help. If you take action and prove that you’re committed, people will be willing to offer advice, referrals, or a sounding board for your wild ideas.
“Being an entrepreneur is going to shake your life. You will go from the kind of person who gets a paycheck every two weeks to the kind of person who only eats what he kills. Don’t worry. It will all be OK. But it will take you naked to the jungle, and you have to come out alive.” — James Altucher, “Skip the Line”
This may be the last new article on Studenomics, so subscribe to my Substack page if you want my newest content. Thank you for joining me on this ride.