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5 Lessons For Finding Success — No Matter What Path Your Life Takes


by Greg DeLine, president and CEO of DeLine Holdings

Life has a way of taking a zigzag trajectory. You can plan for what’s around the corner, and you can have aspirations for the future. But more likely than not, you’ll end up having to make adjustments along the way.

Those of us who have been in leadership positions for long enough realize just how impossible it is to forecast too far ahead. Yet that doesn’t mean it’s meaningless to try to control what you can or to prep for uncertainty. Every entrepreneur can rev up their ability to roll with life’s punches by studying and emulating the traits of successful people who have come before them.

Interested in building your leadership acumen? Take a look at some of the biggest lessons that I’ve learned by the best instructor of all: experience.

1. Nobody has a playbook. 

You’ll hear many “truisms” from well-meaning people who want to give you a map for your career and life path. For instance, plenty of people will suggest that you absolutely must go to college to become a successful entrepreneurand businessperson. But although higher education is an asset and can offer theoretical tools and networking opportunities, it’s unnecessary. Full disclosure: I don’t have a bachelor’s degree (and neither do around three-quarters of business owners, per CNBC and SurveyMonkey research).

This isn’t to say you shouldn’t go to school. By all means, get a degree if that’s right for you. Just know that it’s not right for everyone, and it’s not the end-all, be-all to entrepreneurial stardom. Remember that you can always forge your own path.

2. Humility is an underrated asset. 

What’s missing in leadership today? If you read the news, it’s certainly not arrogance or aggressiveness. Instead, what’s lacking is an overarching sense of humblenessamong the people in charge. Simply embracing humility in leadership will get you far. It will become your differentiator and a value-added part of what you bring to the table. However, showing this kind of humility and compassion in leadership can be hard.

I started my career wanting to always be right, and it took time for me to realize that being able to make mistakes, ask for forgiveness, and understand that leading with your ego isn’t leading at all. Rather, start earning credit by treating others with integrity and respect. Keep your promises, and be true to your word. You might feel like you’re not making progress at first, but you’ll get further in the end than the hothead running the company down the street.

3. Practice transparency and genuineness.

I wear my feelings on my sleeve. Everyone can read me, and I’ve come to appreciate that I don’t have to hide anything as a leader. However, being genuine requires deep introspection and self-acceptance.

When I started my career, I tried selling insurance and then vacuum cleaners. I landed zero sales and wondered whether I was a failure. Then, I had an epiphany: I was a good salesperson, but I lacked passion for life insurance and vacuums. It was a watershed moment because I realized that I had to stay faithful to my calling in order to succeed.

If you’re struggling today, you might simply be doing the wrong things for the right reasons. Step back and understand yourself. Jot down what makes you tick and what motivates you. Once you figure that stuff out, the rest will fall into place.

4. Know when to be a shepherd versus when to be part of the flock. 

Among the common characteristics of successful leaders (as well as traits of highly successful people in general) is understanding your momentary place in the flock. One day, you’ll have to lead your flock. The next day, you might do better grazing alongsidethe flock. Switching between these two positions can be challenging. My nature is to lead the flock, so that’s my first instinct. Nonetheless, it’s not always the wisest move. Therefore, I frequently ask myself whether it’s time to serve or time to lead.

Knowing where to be and when to be there can be tremendously freeing. Plus, your people will appreciate that you can put the team’s needs above your hubris. Don’t be surprised if you see reduced turnover among your crew when you stop demanding all the limelight.

5. Ask yourself the tough questions. 

You might say you’re an honest person. Do you ask yourself the hardest questions of all, though? For instance, would you be able to admit to yourself that you were motivated by greed or envy? Or that you made a snap choice because you were in a sour mood?

Becoming a successful entrepreneur who’s in the top 1% requires you to be totally upfront with yourself. That way, you’ll be less likely to repeat missteps or ignore red flags that your intentions might not be as pure as you’d like to think they are. Part of this lesson involves knowing your personal strengths and weaknesses, so consider conducting a SWOT (or strengths, weaknesses, opportunities, and threats) analysis on yourself. You don’t have to show it to anyone else. Use it as a true reckoning of what you do well — and where you can improve.

Adopting the character traits of successful people isn’t something that will happen overnight — neither will hitting your stride as an entrepreneur. Take the process one day at a time while always learning from those who have been in your position before.


The president and CEO of DeLine HoldingsGreg DeLine is an entrepreneur and philanthropist. Greg has started and owned more than a dozen successful companies. He has a passion for relationships and helping others reach their full potential. In addition to leading various companies, Greg is the president of the board for Phoenix Programs, past president and current board member of Love INC, and a Leadership Circle level sponsor of the Heart of Missouri United Way.