7 Lessons of a Rookie Entrepreneur

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After almost two months of being a full-time entrepreneur, there are a number of first-time experiences, feelings and lessons I’ve walked through that I thought I’d share simply for therapeutic reasons and also because they might help someone else starting out for the first time.

A lot of these particular things I’ve learned may have come up simply because of my personality type and quirks as a human being. Some are most assuredly because I work from a home office. But I think there’s some applicable value in most of them.

So here are six things I’ve learned as a rookie entreprener:

1. It’s a daily roller coaster ride.

Up and down. Up and down. Up and down. [Repeat each day.]

The moment you start celebrating a great victory like a good sales day or a strategic marketing move that actually worked, the next day you’ll be in the dumps again. Customers will complain, something will invariably break, [insert something bad here]. And it’ll rob you of the joy you had experienced the previous day.

I’m not a downer, really. Don’t get me wrong. I am an optimist. I do like to look at the positive and bright side of life. But I’ve realized I need to be my own source of encouragement. It’s got to be internal first, or I’ll take in all the negatives and they’ll start to sink my ship.

Thankfully, I have great partners in all this. They’re extremely encouraging. I have business partners that keep me in perspective and are there when I need to bounce ideas off of them.

2. Self-doubt creeps in.

Because this is all fairly new to me, I doubt myself often.

Am I good enough? Am I talented enough? Did I make the right choice? Do I have the stamina and energy? Is this thing going to work? What happens if … ?

There are few past experiences I can compare what I’m doing to. This is the first time I’ve worked full-time for myself. And I’m steering the ship virtually by myself. I believe in my ideas, strategies and business potential (enough to quit the best full-time job I’ve ever had that included security/benefits and the respect and appreciation of my bosses), but there are times when I wonder if they will actually work or yes, if I even made the right choice.

This happens usually when I’m at the bottom of my roller coaster ride though. So I try to remind myself of where I’m at mentally and even physically. If I don’t remind myself of this, I’ll let that self-doubt consume me.

3. Fear is the wicked sister of self-doubt.

Thankfully, at the moment, because of the environment and atmosphere of my partnership, I don’t have a lot of fears. Particularly, the worst one: finances.

Namely for me, my fear is that of failure. (See No. 2)

4. There are no boundaries, you must create them.

The first thing most people I’ve talked to about working from a home office say to me is: “You’ve got to establish boundaries.”

What they mean of course is that it’s easy to work 90 hours a week if your office is two doors from the bedroom where you sleep at night. And across the hall from your kitchen and living room.

Since I’ve been working insane hours since last March anyway, I’ve had a little bit of experience dealing with this particular boundary. It’s still a work in progress, but I’m starting to get better and better at realizing when it’s time to take a break from “work.”

The best example of this is not checking email right before you want to go to sleep!

But the real boundaries that I’ve dealt more with is …. the ones that are typically built-in at a normal 9-5 job in an office environment.

I’ve always been fairly disciplined, a self-starter and extremely driven, but when you’re working for yourself, you have to establish EVERY boundary that you once took for granted. This might be obvious to you, but it’s just a fact of life for me now.

Things like …. what office hours you keep (I stuck with the one I had so I could simply keep that momentum and routine going). This is just one of many … you could also think about how you dress, how you balance routine house duties with work ones, distractions and interruptions, what happens when friends/neighbors know you work from your home office and disturb your routine, etc. etc.

5. You MUST get out once in a while.

For me, a big priority right now is physical exercise. My commute is now 5 seconds. And the little exercise I got before I started working from my home office is even smaller now.

Working from home is great because I can minimize the distractions I once had in my office. But the tradeoff is … sometimes I forget I’ve been sitting and staring at a computer for three hours. So my legs hurt. My wrists hurt. And my eyes feel like I’m in a fog.

Another thing is …. working from a home office, you can easily get cabin fever.

This is why I have to force myself to get out. There are times in the week when I HAVE to schedule a lunch with a friend, or simply go to Taco Bell and eat. Or just go to the bookstore for a while, or my recent favorite the Apple store (just to look and stretch my legs). All so I can look and be in surroundings that are different from my house.

6. Sometimes it’s just plain old lonely.

Don’t get me wrong … I love and cherish my wife. She is the best companion ever. And I also love the fact that I can pretty much control my office environment (besides the phone, I don’t get too many interruptions, which is such a blessing!).

BUT … when you’re working on something that you helped create for long periods of time. And not too many people in your world or THE world understand the intricate details of it (or even care to), the crickets start to chirp rather loudly.

For example, many of our friends have asked what I’m doing now … what is this new business is all about. After going through this routine a thousand times and seeing people’s eyes glossed over or rolled back in their heads, I realized that no one cares about this business nearly as much as I do.

My family asks and they try their hardest to sound interested. But for about 99% of the people I know … they just don’t get it.

The simplest and well-received answer I give is: I run a web design company. And most people get that (kind of), but it really doesn’t adequately describe what I’m pouring my life into right now.

I really can’t and shouldn’t expect them to love all the details about strategies and new ideas I have. It’s not their passion. It’s mine.

Thus, the crickets chip.

7. But at the end of the day, it’s still a blast.

Most of the previous 6 points have been fairly negative. Heck, I’ll say it … they were negative!

So with this final lesson I’ve learned I’ll share the great positives.

It is indeed … an absolute blast. And I’m learning to deal with all the things I’ve mentioned in a healthy, positive and enduring way.

I’ve realized this is not a sprint, but a marathon …. I’m in this for the long haul. I want to build a business. A good and vibrant business that prospers.

The major benefits I’ve thoroughly appreciated and enjoyed … which also make up for the negatives … are:

  • I have freedom and flexibility in my work,
  • 100% of my time, sweat, blood and tears go into something I own,
  • Most of the time I’ll get back what I put into it, plus some, and,
  • I get to put my ideas into action and have the time to do it.

The bottomline though is … I know that I have entered a brand-new world called entrepreneurship. Most everything is new. And I quickly realized why many people never attempt it … and why some eventually give up. It’s scary. It’s overwhelming at times. It’s a whole world that is pretty much nothing like the working world I grew so accustomed to.

But the fork in the road for me, especially when Nos. 1-6 hit me in the beginning, was when I had to ask myself … will I run away from these feelings and go back to something easier and safer …. or will I embrace this new world, make it my own and conquer it?

… for me, after a moment of reflection, the answer became obvious … I want to see where this roller coaster takes me.

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6 thoughts on “7 Lessons of a Rookie Entrepreneur”

  1. Thanks Chris and Randa!

    Dave, so glad they helped. I think it’s good just to know you aren’t alone. I would think most startup entrepreneurs are going through similar experiences.

  2. Great article. I too am a rookie entrepreneur and through my various business ventures, I have learned so much. I can relate with the article in so many ways. You mentioned self doubt creeping in. I would also like to add that doubt will also come from friends and family. Don’t be discouraged. These people could just be jealous. Keep trying and remember…You don’t need many good ideas, just one great one. Many entrepreneurs failed several times, before making it big (Colonial Sanders of KFC, Conrad Hilton of Hilton hotels to name a few). This is just one example of the many lessons I learned from my business venture.

    As a matter of fact, I wrote a book titled: “Business Lessons of a Rookie Entrepreneur” describing my experiences. Please check the book out by searching the title: Business Lessons of a Rookie Entrepreneur on Youtube (also can search my name). It teaches the lessons I learned while starting and running my own businesses. This book is a no-nonsense approach to starting and running a successful business by teaching you how to avoid making simple mistakes that will “nickel and dime” your company to death.


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