The thing about careers, entrepreneurship, and life, in general, is that you’re always going to make mistakes and learn along the way.
But it’s unwise to only learn from your mistakes: The smarter strategy is to learn from other people’s mistakes too so that you can avoid them and do much better.
A smart person learns from their mistakes, but a truly wise person learns from the mistakes of others.
— Ken Schramm
While I’m not the CEO of a Fortune 500 company, I’ve made plenty of mistakes in my career—corporate and entrepreneurial—and learned many profound lessons from overcoming them. So I want to share the most glaring mistakes I’ve ever made and how you can avoid them to get ahead in your business.
1. Not Quitting Earlier
Now, I’m not encouraging you to be a “quitter”—the kind of person who quits at the first sign of challenges or failure. But when things are beyond repair, you have to know when to give up.
For example, I once worked a job I loathed for 16 months before I quit. Afterward, my life grew exponentially and I had more mental and emotional bandwidth to pursue my goals. But despite wanting to quit for many months beforehand, I delayed for some very common reasons.
First, I didn’t think I could do any better and I believe my job was the best one around. But that was a flawed mindset: I was thinking narrow-mindedly rather than considering the many different possibilities and ways I could use my skills.
Second, I kept thinking my situation could get better if I worked harder and gave 100%. But when I did that, I still struggled. In reality, the company had serious issues and no amount of hard work could overcome those problems.
Things rarely get better on their own. (And if they do, it might take a long time.) Instead, it’s often wiser to cut your losses and find something better.
This lesson has given me a lot of peace of mind as an entrepreneur. There have been times I had to fire a client shortly after starting a contract because they didn’t uphold their responsibilities and made life difficult for everyone. But rather than holding on, I ended things quickly because I knew things wouldn’t get better and I had faith that I could find better opportunities.
2. Not Watching the Warning Signs
I used to be blind to warning signs because it was so ingrained that, if something was wrong, the solution was to work harder. Well, sometimes that’s true, but it really depends on the situation.
Look around you. Are there inequalities within the workplace? Is there a lot of turnover or restructuring? Are overall numbers trending down? Is there a sudden change in communication?
Read the writing on the wall. Those are all signs that there are deeper, systemic problems and that you might need to jump ship before it’s too late. As an entrepreneur, this is critical so you’ll avoid being blindsided by sudden changes in your cash flow or clientele.
3. Not Asking For Help
In all honesty, it’s hard for me to ask for help because, growing up, I learned that asking for help is a sign of weakness. It means you failed and, oh, by the way, no one really wants to help you because it’s a cold, mean world out there. (I’m serious—this is exactly what I was taught.)
As you would imagine, it took me many years of hard work to overcome this and I still struggle with it.
Learn from my mistakes. Never be afraid to ask for help. Sure, don’t become a freeloader, but if you’re looking for an opportunity, let people know. If you want to be connected, let people know. And for the love of God, thank them if they help. (You’d be surprised how many people don’t.)
Ramit Sethi once said that “the best $20 you’ll ever spend” is to take a successful person out to lunch and ask them questions—and he’s right. I’ve done that numerous times as an entrepreneur and I’ve learned more than any article could teach me. They shared powerful insights to help me grow my business and make better decisions down the road.
4. Not Listening to Cultural Issues
Earlier, I mentioned the job I hated had serious issues. In hindsight, there was widespread favoritism, conflicts of interest, cheating, bullying, and more. (Fun fact: This anonymous company gets hit with many lawsuits.) While it was frustrating to be in that environment, I thought I could avoid the unethical bullshit and still succeed.
Boy was I wrong.
Trust me, nothing crushes your soul like working for someone you feel dirty about. You’ll feel like you’re violating your values. Worse, the longer you stay, the easier it becomes to compromise your ethics.
Leave before it’s too late.
As an entrepreneur, listen to the culture of your own company and the ones you work with. For example, I’ve worked with clients who seemed nice on the outside but were mean on the inside and doing shady things—and I ended things as soon as I could. Your integrity is all you have.
5. Being Afraid of Self-Promotion
I’ve long had problems with self-promotion: I thought it was arrogant, gaudy, and conceited, but in reality, the real problem was that I had painfully low self-esteem and didn’t feel comfortable with self-promotion.
Here’s a reality check: If you don’t toot your own horn, no one will toot your horn for you. You can be the best in the world at what you do, but if no one knows you exist, it doesn’t matter.
As an entrepreneur, learn how to showcase your accomplishments. One simple strategy is to keep a list of every little success. If you did a great job on a project, created a great idea, or got a compliment, keep a running list so you remember. (This will also be useful when you write your testimonials, case studies, and more.)
6. Not Learning How to Negotiate
Not knowing how to negotiate can cost you thousands of dollars in extra income every year. And when you add that up as well as the extra money you could’ve earned by investing it, that could be over $1,000,000 in missed earnings over your lifetime.
Bottom line: Learn how to negotiate. There is no excuse.
By learning how to negotiate as an entrepreneur, I regularly was able to command the highest rates of any other vendor despite not necessarily being more skilled. The only difference was that I knew how to respectfully ask for more while everyone else settled for less.
7. Listening to Bad Advice
There’s a lot of bad advice out there. But while following bad advice is like shooting yourself in the foot, following good advice can transform your life. So how do you check if you’re getting good advice or not?
Simple: Analyze the person who’s giving it to you.
If you follow someone’s advice, you’ll probably end up exactly where they are. But if they’re not doing what you want to do or living a life you want to live, how would they be able to give you good feedback? For example, if you get business advice from someone who’s never started a business, how would they really know?
Instead, ask people who’ve done what you want to do or have coached people on how to do it. Also, imagine trading places with them so you can also assess their character and integrity. Because while some people might be successful at their job, if their personality is questionable, their advice might be too.
I spent a large part of my life listening to advice from my parents, my family, or random authority figures, but none of them had a business—or lifestyle—that I liked (even a little bit). As a result, I was regularly struggling to get ahead and feeling miserable.
It wasn’t until I started listening to people who actually did what I wanted to do—and thus, knew what they were talking about—that I finally started to make real strides in my business.
And from that point on, my life was never the same.
Good luck with your journey.
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