The Entrepreneur’s Journey: Slowing Down and Why Grandma’s Always Right.

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By Daniel DiPiazza

Are entrepreneurs always dissatisfied?

It’s hard to stop and bask in your own achievements. It’s why we strive to build a tool that shows you how far you’ve come to motivate and inspire. Daniel DiPiazza, who works with plenty of young go-getters brimming with restless, entrepreneurial spirit, reminds us about the importance of learning to relax and appreciate your own hard work.

Grandmas have an uncanny way of presenting elegant solutions to life’s most vexing conundrums — wisdom without tripping the alarm system. Every day, mine would take me on a short walk from our suburban duplex to the small office where she practiced law at her own firm. I always thought the walks were social outings, but looking back, I know now they were opportunities for her to teach me her life philosophies.

At seven, I just wasn’t ready for the sophisticated dose of grandmotherly psychological judo I received, but her words stayed with me.

“Do not be beholden.”

We talked a lot about entrepreneurship, self-direction, motivation, and self-image on our walks. These may seem like heavy topics for a first-grader, but I am certain I would not be the person I am today had we not had these talks. One thing she said to me still rings crystal clear:

“There is no greater pleasure than working for yourself. You do not want to be beholden to anyone else. Chart your own path.”

Photo: Cornelia Kopp

As I got older and started working, something didn’t feel right. I never really felt like I fit in anywhere that I worked. At first I thought it was the job. Or the boss. Or the co-workers. Or the uniform. Until I ran out of “or’s”.

That’s when I realized — it was me.

While I had hated every single job that I’d ever held, all that time the entrepreneurial bug had been living inside of me, feeding off my ambition and slowly growing into a gigantic monster that couldn’t be tamed or assuaged, even with the promise of a decent salary.

So I broke out on my own the minute I could, and I haven’t looked back. Happily ever after? Not quite.

The Double-Edged Entrepreneur

The entrepreneurial spirit is an immense gift and equally colossal curse.

On the one hand, you have complete autonomy over your livelihood. You’re practically Django Unchained. Exciting things are bound happen. On the other hand, now you’re completely exposed to the disappointment that comprises the ugly flipside of that excitement. You are 100% naked and at the mercy of your own endless ambitions.

What most of us with the entrepreneurial spirit don’t realize upon embarking on this voyage is that we will never be satisfied. Our greatest efforts will usually never be enough in our eyes, and even when we do accomplish something, we will immediately be looking for the next rush of excitement in another endeavor.

There’s always another peak to summit. Whether it’s attracting more customers, creating a more perfect UX, generating more profits, or doing all of the above faster. As entrepreneurs, our satisfaction always seems to be fleeting at best.

I don’t think true satisfaction will elude us forever, but we have to change our perspectives. We have to change our definition of success if we ever want to be truly satisfied.

What to do about our dissatisfaction:

Stop caring so much about how well your business does.

Yes, I know what I just said. Hear me out.

Stop using business success as a measuring stick for life’s progress. It’s unhealthy and only leads to anxiety. Business will come and go. Our happiness and peace of mind must be a constant force in our life, no matter what is going on in the boardroom.

Start looking at businesses as tools to create more freedom of choice and opportunity for our loved ones and ourselves. After all, that’s why we started this entrepreneur journey:  freedom. From this moment forward, you shall no longer be chained by the very creation that was meant to give you freedom.

1.     Take back your time.

Start by taking back your time. You actually make your own schedule. Stop letting other people’s agendas dictate how you spend your day. Stop checking your email every 10 minutes waiting for someone to tell you what to do next, you maniac.

Have some self-direction. Have some discipline. Begin your own personal renaissance. Remember that one of the biggest reasons you avoided the 9-5 is so that you would have more time to taste the fruits of life. Why aren’t you tasting them?

Stop being afraid of deep recreational pursuits. Learn a new language with purpose and focus, then take a trip and really test drive it. Take up a hobby that you’ve been putting off for years because it wasn’t the right time. I’ve been stop-starting my martial arts training for ten years. This year, I’m going to take both my own advice and a page from Nike’s book. I’m doing it. Period.

Photo: camdiluv

Begin your entrepreneur journey full of new milestones and mistakes that have nothing to do with earnings reports. Those reports will still be there when you return.

2.     Turn your business brain off and engage others.

If you’re like every other entrepreneur on the planet, myself included, your brain is a 24/7 storm of creativity begging to be expressed. This is because we invest our entire lives into our endeavors, and they are usually things that we already like to do. At Rich20Something, I get to do all the things I’m most passionate about: writing, designing, coaching and computer programming. Trust me, I understand.

The people that we care about love us, but the don’t necessarily love our creations as much as we do. They just want to see us happy. So let’s have a little self-awareness. Next time you’re out at dinner with your sweetie (or your friends, or your parents), give them the pleasure of not talking about your genius implementation strategy, or the software patch you’ve developed, or the new client you’re so close to landing.

Shut off your start-up brain. Find new things to talk about. And for God’s sake, listen for once. Actually engage and respond to people instead of running business models in the background and giving them the auto-you. Be there.

3.     Stop worrying and enjoy the entrepreneur journey.

Worry is the ‘trep’s constant companion. How will this launch go? How will people like what I’ve worked so hard to create? Will we get that VC money? Will people even notice us? Will they even care? Most importantly, how will all of this affect the way I feel about myself?

These questions race through our minds on a daily basis and oftentimes, rather than quelling them, we look for evidence to confirm our worst fears.

Success runs deeper than fear and worry. The truly successful people out there know that no matter what, they are going to come out on top. When things don’t work out, they regroup, retool, and reimagine so that the next one does, until they produce the outcome they want.

Stop worrying so much about your current project. Instead, focus more on how far you’ve come and how excited you are to have the opportunity to try your business ideas out. The results will come with time.

Learn to actually enjoy the process.


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