18 Things I Learned In My First 18 Months of Entrepreneurship

This month is the 18 month anniversary of my website and blog. In September of 2013 I finally launched what I had always dreamed of: my online wellness business. Coming from Corporate America, this was a scary thing.

I used to keep a Mark Twain quote up in my cubicle. I can remember staring at it during stressful afternoons, and daydreaming of a life outside of the “normal” 9-5:
“Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”

When I launched my wellness business, I kept this quote in mind. And now, 18 months later, I can tell you that my surroundings are a little bit more familiar, but the unknown waters still exist. The exploration continues…

18 months, 80 blog posts and recipes, over 25 online guest features, a self-created online wellness program, a self-published cookbook, inspirational business partners, and countless amazing clients later, I have learned so much. Read on for the 18 things I have learned in my first 18 months.

18 Things I Learned In My First 18 Months of Entrepreneurship:

1. The “little things” feel so incredibly rewarding.
The smallest things can bring the most happiness. A new email subscriber, a new social media fan, a new inquiry about my online wellness programs, etc. They may seem like small things, but being in charge of everything in my business, they feel like gigantic steps forward. There’s something about receiving 100{54c12dad2cc2b53ae830e39915b1a3e70288dbcbbeb8bbf8395437c5dc3c512c} of the rewards of your efforts that is incredibly satisfying. Of course, there is a flip side to this…

2. It’s far too easy to take things personal.
While the good feels great, the bad can also sometimes feel worse. Losing a client, getting an unsubscribe, etc. It’s way too easy to take things personal, so I remind myself that it’s impossible to please everyone all the time. And in the end, it’s not about helping everyone, it’s about helping those that want it.

3. Comparison is an emotional & business downer (note to self: don’t do it!).
“You can’t compare your beginning to someone else’s middle.” -Unknown. Everyone has a different story and a different starting off point. I learned early on that any comparison to others needs to stop, because as Theodore Roosevelt so eloquently pointed out, “Comparison is the thief of joy.”

4. Purpose must be the foundation of every business.
When I first launched, I simply wanted to help others get healthy by providing easy plant-based recipes, tips for health, and through my online wellness programs. But as my wellness business progressed, I realized that what I do is bigger than that. Providing support and motivation, and inspiring others to truly live their best life is my life purpose.

5. Staying healthy is key for high-productivity.
Proper sleep and nutrition is even more important now than it was when I was in my 9-5. I can remember the mornings at the office after one-too-many glasses of wine. I would go through the motions and make it through the day, but those days don’t exist anymore. I can’t “go through the motions” now. In order to stay productive, I make it a priority to get 8+ hours of sleep, get my greens in, and take my supplements. Healthy Jess = Productive Jess!

6. I’m the worst AND best boss all at the same time.
Confession: I have “shiny-object” syndrome. I’m easily distracted and move quickly from project to project without finishing. As my own boss, I let myself do that, and I really shouldn’t. However, when it really comes down to the wire, I know how to create an action plan and buckle down. So I’m overly lenient (bad), but results-oriented (good).

7. Sleepless nights still exist.
I thought lying awake at night would diminish, but to be honest, I don’t think it ever goes away. Pondering about our future is a normal thing, the difference is that the thought process has changed from worry to uncertainty. And I don’t mind uncertainty. But the BIG change is that…

8. Mornings start with a smile (and a buzz of excitement).
Whereas I used to wake up with a feeling of uneasiness, I now start my day with the satisfaction that I am working towards my passions. I get excited to start a new blog post, finish up a project, follow up with a potential client, or mentor a new business partner.

9. Waking up without an alarm clock is a beautiful thing.
THIS definitely helps with my morning positivity. Naturally waking up without the beep-beep-beep of an alarm has to be one of the biggest perks of being an entrepreneur. And not having the time constraints of an alarm also allow me to work late at night (something I do often), because I know I don’t have to face that 5am alarm.

10. Time is the most precious resource.
“Time is more valuable than money. You can get more money, but you cannot get more time.” -Jim Rohn. There is no software program, training course, or phone app that will take the place of the #1 most important thing in my business: Time. And not just time, but using time wisely.

11. Multitasking = Unproductive.
I used to love labeling myself as an “excellent multitasker”. When I was applying for corporate jobs, I had it listed as one of my top skills, and I prided myself on being able to do multiple things at once. When I tried to multitask in my business, I realized it was impossible. Doing two things (or more) at one time only leads to one result….not getting either of them done. Focusing on single-tasking was one of the best things I ever did for my business.

12. Perfection is an entrepreneur’s worst nightmare.
Let’s face it, we all have a little bit of perfectionism in us, am I right? I’m the type of person who has tons of ideas swirling in my head, but actually taking the time to create those ideas into something tangible is challenging. It’s in my nature to want everything to be perfect before I do anything. But perfectionism is a biz KILLER. A mentor once told me, “If you are not embarrassed by the first version of your product, you’ve launched too late.” So I launched a product (that I originally told myself wasn’t done), the next day, and had the biggest sales week of my life.

13. Social media is a love/hate relationship.
Don’t get me wrong….being able to run a business and interact with others online while I’m at home and in my PJ’s is an amazing thing, but it’s a catch-22. It’s really easy to stay connected, so it’s also not easy to disconnect. Sometimes I yearn for my 9-5 days when I didn’t feel guilty for not logging into Facebook for days (or even weeks).

14. Failure is unavoidable.
I once spent nearly 6 weeks putting together a launch sequence and new program. Videos, emails, PDF’s, everything. When launch day came and had no signups, I figured everyone was just procrastinating. But then doors closed, and I realized that 0 people purchased the program. Ouch. Not going to lie, it was disappointing. The next day, I logged into Amazon and John Maxwell’s book popped up, “Sometimes You Win, Sometimes You Learn”. YES. Big lesson learned! The good news here is….

15. Success feels sweeter after failure.
There’s something about a personal comeback. It feels like Rocky against Apollo. Personal redemption and success feels that much sweeter after experiencing a failure. The next launch I completed proved that the previous failure was more like a glitch, or a bump in the road.

16. Ignore the doubters.
Yes, there will be doubters. My own husband doubted me at first. And a lot of my former acquaintances as well. But I knew my vision, and I stood true on my direction. You have to remind yourself that you are capable, worthy, and deserving of your success. And then go out there and get it. And you also must…

17. Surround yourself with a like-minded tribe.
A like-minded tribe will not only cheer you on and prove the plausibility of success, but will also identify with the lows and help to pick you back up. I love being surrounded with other smart and soul-centered entrepreneurs, and that’s why I created my Savvy Biz Club, a free group for other biz owners to interact with those who share the same challenges. A like-minded tribe is absolutely critical to success.

18. Being a business owner is scary, exhilarating, and gratifying all at the same time – and I wouldn’t trade it for the world.
There is no guaranteed steady paycheck and that can be scary…but I have never felt more alive and filled with wholeness and purpose. Being able to chart my own path and create my future is the best feeling imaginable. Entrepreneurship is truly an incredible way to make a living.

Jessica Lauren DeBry is a Wellness Entrepreneur and Online Biz Mentor. Join her FREE membership club specifically for Smart + Soul-Centered Entrepreneurs at SavvyBizClub.com to access exclusive videos, webinars, and resources.


Erin shows overscheduled, overwhelmed women how to do less so that they can achieve more. Traditional productivity books—written by men—barely touch the tangle of cultural pressures that women feel when facing down a to-do list. How to Get Sh*t Done will teach you how to zero in on the three areas of your life where you want to excel, and then it will show you how to off-load, outsource, or just stop giving a damn about the rest.

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