The Leap

Finally quit my day job…here’s what I’ve learned (so far)

Dave Anderson
5 min readFeb 14, 2014

I made the decision to leave my comfy corporate job in favor of being an entrepreneur in April 2012. I didn’t hate my job, or the people I worked with, or the 35 minute drive to work or even my cubicle. I did however, hate the thought of never reaching my full potential. The mere thought of having to look back at my life and say to myself or my future children that I never tried it, absolutely horrified me.

So, I knew I had to take the leap, but I still had lots of questions. Is this the right time? Is there ever a right time? What will my friends and family think? What if I fail? What if I succeed?

For those who are considering taking the leap, here are my thoughts on those questions…

Is this the right time?

No. There’s never a right time. I don’t even know what ‘right time’ means? Is it after you’ve made enough money? Or maybe after one more promotion? If you’re waiting on everything to be perfect, get comfortable being comfortable because you’ll never leave. In my experience, perfection is only realized in hindsight. I’m not advocating any rash decisions or a lack of preparation. But, at some point we have to stop analyzing and do. Or else, we’ll just continue to move the goal post.

What will people think?

Who cares…kind of. Whenever I need to make a big decision, I bury myself away for some period of time and critically think to myself first, then I seek counsel. I start with my wife (because she’s awesome), then my dad, then other people I trust. The problem is, when it comes to quitting, unless you’re surrounded by other entrepreneurs, the people in your circle just might not understand. I love my dad to death and he usually gives pretty darn good advice, but he worked for the same company for 40 years then retired with a comfortable pension. What does he know about quitting? When I told him I was leaving my well-paying job that I went to college for to start my own business, he couldn’t comprehend it…it just didn’t register.

The point is, don’t expect everyone to: 1) understand your idea/vison right away, and 2) agree with you. Your decision should be based on collective opinion that starts internally. Although, if you believe strongly and everyone you consult disagrees with you, there is a chance that you’re the one contrarian that changes the world.

Btw, my dad eventually came around after I shared my full vision and my reasons for doing it.

What if I fail?

You will. But, it doesn’t make you a failure. If you think you’re going to quit your job, make a sweet product everyone loves, see hockey-stick growth your first year, IPO, buy a yacht and sail into the sunset to personalized theme music without ever having tasted defeat…please scroll up a few paragraphs and seek better counsel.

Life is composed mostly of little failures and successes and they should be treated just the same. How many times has a failure caused you to succeed or vice versa? We all have to learn to deal with failures without allowing it to define us. Stay focused, listen to feedback, adapt where necessary and be tenacious.

What if I succeed?

Embrace it. But, don’t let it distract you. First of all, only you can define success for yourself. Just as failure shouldn’t define you, having a success or two shouldn’t throw us off course either.

Ok, I’m going for it. What do I do now?

Create a safety net — My wife and I avoided debt and saved for a few years prior in preparation for me leaving. It really helped.

Don’t burn bridges — You never know what’s going to happen. My old company now wants to be a pilot customer because I left on good terms.

Establish a support system— Join a coworking space or attend meetups. Myself and a few partners opened a coworking space (Bamboo Detroit) a few months back and the community support has helped me immensely.

Embrace your fears— Rational fears of disease and violence keep us alive, but we’ve got to address irrational fears that inhibit growth. Since ambiguity is frightening for all of us, it helps to develop a plan to minimize uncertainty as much as possible.

Fall in love with risk— I decided that I’m more uncomfortable with not reaching my full potential than I am with taking risks. This quote from my friend Scott (co-founder of Ginkgotree) sums it up…

Want to change the world? Avoid staying comfortable as much as possible. Fall in love with risk, boldness, and making people uncomfortable…the rest will follow.” ~Scott Hasbrouck

What I’m up to now

When I committed myself to being an entrepreneur, I set a goal to leave by a certain date. I went to every meetup/networking event I could find. I helped other startups. I started a business for myself — great idea, but it failed. I spent every night and weekend I could working toward my goal. Then finally in May 2013, some partners and I started a coworking space, Bamboo Detroit — a members-only collaborative workspace for entrepreneurs. We’ve grown it to over 35 members, serve as a resource to the community and have been featured nationally .

I missed my goal of quitting by May 2013 by a few months, but who cares I’m here now. I never want to feel the crippling comfort of steady income and daily repetition again. I’ll take calculated risks until I’m able to empower others to do the same. Just to sound as idealistic as humanly possible, I intend to change the world…in whatever way I can. I am now Chief Marketing Officer of the tech-startup, backstitch — an online platform that automatically builds personalized streams of content based on your interest. I’m ecstatic to work on my passion — my love of technology at backstitch and my love of community through Bamboo Detroit!

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Dave Anderson

CMO of @backstitchapp | Co-founder @bamboodetroit | #entrepreneur | #technologist | #Detroit enthusiast | dog lover