I'm Afraid...

Third time I've had this conversation, this week alone.

The goal is expressed as:

I want to take this brilliant business idea, and make it my own.

The dilemma:

I'm afraid of leaving my steady "stable" income stream (aka: my day job).

My answer:

Ignorance is the parent of fear.

Yes, that's a Moby-Dick quote. :-)


I usually express my answer with a smile.

If you told me, eight years ago, that I'd be running my own business today. I would have said you were crazy, shaken my head in disbelief, and tried to distance myself from you; you crazy crackpot.

The Turning Point

My turning point was eight years ago, almost to the day. I remember a job interview.

We're sitting in a large conference room; mostly dark, except for a few chairs; two across from mine, and no table in the middle. Outside the office were unassembled desks, and a few large exercise balls. Construction and remodeling were underway, and in this dimly-lit room a single overhead light glowed above my head. My back was to the door.

For the past ~45 minutes, we'd been casually chatting. I'd already spoken with the founder, CIO, and awkwardly waved at a couple software developers while adjusting my too-warm and tight-fitting suit jacket. Things seemed to be going alright, but as with most interviews, it was difficult to tell.

At this point I'm chatting with the head of HR, everyone else had left the room. Talk was fast-paced, and after a few standard questions, she asked me:

We're a small company; a startup. We have solid funding for a few years, but there's no guarantees. You're coming from pretty traditional employment; first a government position, and now a sysadmin for your current company over the past seven years. Coming to work with us, what's your biggest fear?

Again, talk was fast-paced, I responded without thinking:

Growing up, I often didn't know where my next meal was coming from. My mother had plenty of excuses for why she didn't work, and my father was, with exception of a modest monthly state-mandated check, non-existent. My greatest fear, was repeating that cycle; not knowing what/when my next meal was, or where my next paycheck was coming from. I'd collected a regular paycheck since my 14th birthday, and I don't intend to stop that now.

Mindy (the interviewer) just sat there in silence. After what seemed like forever, she promptly stood up, tersely said "Ok, we're done!" and walked out of the room.

I couldn't believe I said that. Between the long silence, and her terse departure, I nearly shit my pants.

The Process of Change

Apparently, my answer also didn't hurt anyway; I got the job, and we've worked together in various capacities over nearly the past decade since.

Generally, it was from that interview experience, I'd begun to reconsider my childhood "fear"; revisiting the moment many times over the past eight years.

The Five Year Mark

A few months ago, I passed the five year mark; I haven't collected a "regular" paycheck in over half a decade, but I'm also happier now than I ever was as an employee.

The Path

The past 5-8 years have not been easy. I was diagnosed with narcolepsy and also watched what little hearing I had, almost totally disappear. While medical bills (with insurance!) gobbled over $40,000 of savings along the way.

I also married a wonderful partner, purchased a 2nd house, built a small metal shop, and finally took cycling seriously enough to boast a few multi-100-mile solo badges. Even if family and friends rescued me from the end of a 300 mile ride :-)

Oh, and I built a fully N+1 redundant datacenter, which continues to grow: my original goal, and the source of today's bread and butter.


Yes, along this journey I've been afraid of failure. I'm learning, slowly at times, to not allow fear to control me.


If you're thinking of venturing out on your own. Knowing what I know now, these are what I suggest you be mindful of:

  1. Money. Having depleted savings on medical expenses, I started the business with a $0 bank balance. I sold a platinum and gold coin, traded time for needed equipment, and converted a few personal assets into business tools. Those were enough to kickstart a low-capital business. Do you have sufficient resources within your support networks, to pull this off?

  2. Planning. Having been laid-off, I didn't have the luxury of planning. Through a federal level self-employment assistance program I established just enough cashflow to cover the major bills over the first few months. My wife (girlfriend at the time) and I each maintained own health insurance along the way (2nd to rent, in monthly costs). With her focused on completing grad school, and me on bootstrapping the business, our regular meals were largely due to the generosity of family. The federal grant lasted just barely long enough (6 months) for me to establish a cashflow foothold. How much cash do you have in reserve?

  3. Focus. At one point, I intentionally overshot equipment/resource reserves to accommodate an aggressive "growth" phase. Life threw my wife and I a few curveballs, which distracted me from the core business and delayed monetization of related investments. Consider the personal and professional costs of distractions, and of scope creep.

  4. Marketing. I still suck at this. At this point, my business has the tools, infrastructure, and automation in place to support about four times its existing volume. While growth has been consistent/steady, what's currently holding me back are my terrible marketing skills.

  5. Skills. With over 12 years of relevant experience at the time, I had enough experience to accomplish my technical goals. Although if you don't have the relevant technical experience for what you're doing, then consider where you'll obtain these essential skills alongside learning how to establish, run and build a business. Establishing and running a business is an all-consuming process in itself.

  6. Discipline, Time & Work Ethic. I was already accustomed to 10-12 hour work days. This worked well for me, because of the initial bootstrap time required, and because I already understood where my personal point of diminishing returns is. Do you know how much you can genuinely put into your business? Are you sure?

  7. Product. There's always someone that can, generally, do my job better than I can. Its in the niches where we small business owners thrive.

In Closing

If you'll take notice of the main lessons here. There's one missing point; the technical merits behind why I started the business are largely overshadowed by the realities of HR, PR, and AP/AR. Are you ready?