Why You’ll Never Be Happy If You’re Always Searching for More

by Derick SullivanJanuary 16, 2023


Opinions expressed by Entrepreneur contributors are their own.

As someone who has focused on building businesses and wealth for the greater part of two decades, I’ve almost always been focused on more. More clients, more employees, more services, more investments, more franchises; I’ve always been focused on more.

As entrepreneurs, we generally want more — and on the surface, there’s nothing wrong with that. Getting more clients allows you to hire more employees and provide more value to the world in general. More clients and employees, if done right, will create more money and more of an ability to provide for your family and invest in other opportunities. Those investment opportunities can provide other jobs, income, housing and money for everyone involved.

At a glance, more is generally better. The pursuit of more isn’t immoral or wrong — but the pursuit of more can have other far-reaching effects, some of which can cause a negative impact on your life, or at least I’m finding that it’s causing negative impacts in mine.

Related: 4 Things Science Says You Can Do to Be Happy

Why don’t I feel like I’m enough?

In a recent counseling session, I discovered that my pursuit of more was creating a feeling of “not enough” for both myself and my wife. I can only assume it’s also spilling into the feelings of my children as well as other people that I care deeply about.

Coming from humble beginnings, I’ve always had a mindset of consistent excellence. If I’m not building, my legacy is slowly crumbling. So I’ve been focused on building businesses, our podcast, our mastermind, my investment portfolio and myself into more than I was yesterday.

What I’m discovering is that my constant pursuit of more has created a restlessness for both myself and my family that’s not healthy — and I’m not practicing what I preach to those that I coach. To me, family should always be the most important thing in life and providing for your family should be the top priority. I believe I’ve done that well as a business owner and I believe that I’ve created a life for us that I wouldn’t have otherwise without a mindset of pursuit.

What I’m also discovering is that what got me here won’t necessarily be what gets me where I want to be in the future. The pressure I’ve been putting myself under to perform and become better has leaked into other relationships. While that pressure of more has been great for my business partner and me to build Easier Accounting into an eight-figure business and create a successful podcast and mastermind group, it’s not facilitating the relationship I want or need with my wife. She feels my constant want for more and feels as though she’s not enough for me.

Related: Want to Be Happy? Stop Doing These 10 Things.

What am I doing about it?

While I still want to pursue new endeavors, I’m putting a pause on them for the next three months. I’m taking the time to reevaluate what it looks like to believe that I have enough. I’m taking the time to be grateful for what I do have and the life I have built for myself, my employees and my family.

I truly believe that it’s not a bad thing to want more, to focus on building and to create value for society. It’s a noble endeavor that takes sacrifice and its effects are far-reaching — bigger than we might ever know as business owners. But there comes a point when your pursuit of more becomes more than just a virtue or an action. When it becomes a part of your personality, it can create deep-seated feelings of inadequacy for yourself and for those around you.

As you build in business, you generally level up your network, or at least I have as I’ve invested in masterminds and built my network and relationships with high-level business owners. Comparison crept in and what once felt like a lot, no longer felt like it was enough when I compared what I had built with what others had built or were building.

Putting yourself around business owners that are doing more is highly beneficial when you’re looking to build your own business, especially when you’re starting out. You often hit glass ceilings and seeing what others are doing allows you to push past and break those glass ceilings. It’s the often-cited Roger Bannister effect. The brain sees that it’s possible when others demonstrate that it is.

That demonstration is super powerful for many aspects of business, but when you allow it to creep in and comparison becomes rampant, it can become detrimental.

It brings to mind a Kurt Vonnegut poem written in 2005 that recounts the story of him and another author at a party of billionaires on shelter island. Kurt asserts to Joe Heller, “How does it feel that the host made more yesterday than your book ever did?” Joe responds, “I’ve got something that he’ll never have.” Kurt questions, “What’s that?” Joe sums it up perfectly… “The knowledge that I’ve got enough.”

I’m learning that what I have can be enough. I’m learning to be grateful for all the hard work I’ve put in to get where I am. I’m learning that taking the time to smell the roses now might even allow me to create bigger things in the future because I will be more present and aware of opportunities that come my way.

Related: Yes, You Can Be Happy While Pushing Yourself to Success

What I’m learning and what you can do if you don’t feel you’re enough

The biggest takeaways I’m learning about myself through this process of self-exploration are two-fold…

  1. Money will never fill the hole inside you. Money can make life a lot better — and it’s not wrong to pursue money — but there was a time when I thought money might fix all my problems. I’m learning that money sometimes amplifies the problems that we think it will solve. Jocko Willink talks about creating the reflex of labeling any challenge as good, so I’m viewing the awareness of still not feeling like I’m enough as a good thing. If you’re not feeling like you’re enough despite seeing successes and creating forward progress in your life, the first thing you can do is view it as a good thing. You can view it as an opportunity to find out what it’s going to take to be enough for yourself and why you’re feeling this way. Take time to get to the root, it’s a good thing that you’re aware of it.
  2. Comparison is either your friend or your enemy, and it’s all about who you compare yourself to. If you find yourself comparing yourself to others, it’s a slippery slope that can end up with you never feeling like you’re enough. The grass is always greener on social media than it really is in real life. Compare yourself to the prior versions of yourself, look at how far you’ve come and be grateful for the opportunities to become better. Reflect on how you once wanted to be where you’re at today and be proud of the accomplishments you’ve made along the way.

At the end of the day, I’m still learning how to be okay with what I have, even though I know I have built a life I should be proud of. Most importantly, I’m relearning to only compare myself to who I was in the past and focus on being grateful for the changes that I’ve made to become the person I am today — and hopefully, this insight helps you do the same.


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