When The Entrepreneurial Honeymoon Wears Off…

If you work a job right now but want to be an entrepreneur… I totally know the feeling you just know is waiting on the other side of fence. You can already imagine all of the freedom you’ll gain, no more alarm clock in the mornings nagging you to wake up, no more punching a clock, no more answering to “the man”.

It’s paradise being your own boss.


I’ve started several businesses and every time I do… I always have this newfound euphoria that comes along with starting up something new.

It’s exciting. It’s fresh. It’s new. New is good. Our minds react to new by slamming our brains with endorphins and other fancy medical stuff I’m not qualified to rattle off that make us feel awesome.


… it wears off.

It always wears off.

Sometimes it lasts longer than others… sometimes if you structure your business right and architect the business to inject new fun challenges in it you can replicate that feeling… but the Entrepreneurial Honeymoon wears off.

But, before you get all down in the dumps already… it’s NOT a bad thing.

A business is kinda like a marriage.

And if you’re married you know that the honeymoon there wears off too… and marriage takes work. But as the marriage grows… if both sides are always working on the marriage to grow, to keep things fresh, to be honest with each other (and ourselves), to work toward exciting and fulfilling life goals together… the marriage gets stronger and more powerful. Yes, there are ups and downs… but if you work at it… it strengthens.

Your business can be the same.

But don’t go into business if you think it’s all going to be roses all of the time.

Those very things that I thought would be flat out AWESOME as an entrepreneur starting out… were the very things I ended up DREADING over time.

Waking up at 9:30 in the morning and starting work at 11am soon became completely draining and unfulfilling.

Being “able to work” from anywhere (since my startups have always been online based companies). On vacation in Hawaii? Awesome, I’d work an hour or two in the mornings. Sounds cool… but it’s even cooler to be fully present in the moment rather than thinking about work.

Being able to work from home sounds great. And it can be! But it soon became isolating, unproductive, uninspiring, and an easy way to always be a couple steps away from “the office”… which for me turned out to be a bad thing. I’d find myself disappearing upstairs to “check on something” far too often… which set my mind in a perpetual hamster wheel of “work-thought” (I made that word up, but you know what I mean).

So how do you grow a business that thrives, is exciting, fun, insanely profitable, fulfilling, and fresh long after the honeymoon period?

It’s not simple.

I’d be lying if I told you there’s any company that will always be all of those awesome things.

But here’s a few things that have worked for me… especially with Carrot, software company that’s growing fast here locally.

Have very specific goals that actually mean something to you… not just monetary. Money is only a huge motivator when you don’t have any. When you have it… it is a terrible motivator. Find something you truly care about and mix that into the goals for the impact your company will make.

Surround yourself with good people that are a perfect “culture fit” for how you want to live your life. If you don’t have employees, find an office where you can rent a desk and work around people you want to hang out with. Brainstorm, share struggles and successes. It’s magical.

Create 30 day challenges. If you’re not improving you’re withering away. Put fun personal and business challenges in place each month that push you to execute something new fast. This helps keep things fresh and growing… never boring and shrinking.

Being your own boss is awesome.

But if you don’t work at it… it can also be one of the most isolating and stressful experiences you go through, if you don’t take deliberate steps to keep things interesting, new, fresh, and growing in a meaningful way. The choice is yours… get bit when the honeymoon wears off… or put things in place so you’re always keeping things fresh and challenging.

Follow me in my entrepreneurial journey to live an epic life and learn how to live yours!

Connect with me on social media. I'd love to see what you're up to... and I post what I'm up to on a regular basis on FB and Twitter... so hit me up!

Leave a Reply

Your email address will not be published. Required fields are marked *