Last week, MIW Jefe, Lavontay Santos posted a meme in Slack celebrating the hustler’s journey of working a job, planning their escape, and becoming the business owner they dreamed to be.

This Fall will mark the 20th anniversary of me starting my first enterprise. A photography studio I ran with a friend of mine while still working my good paying job as a software engineer.  I always had the bug to be a business owner, and would lay awake in my bed at night thinking about Bill Gates and how I could found a Microsoft. (Yeah, I know, how many 7 year olds knew about Microsoft?  I would sleep with the manual for GW-BASIC.)

After seeing Lavontay’s post, I thought about my own hustler’s journey and how I arrived here, after starting three ventures with varying levels of success and selling one. The meme made me reflect and remember what it was like to start a company while working, and trying to make it into a self-sustaining model.  What I remembered was, “I would never do that again.”

The reality is that most of us don’t have the capital to just go into a venture.  Many of us, myself included used money from our 9-to-5 to fund materiel, infrastructure, and human resources to execute our first venture.  For most of us, loans are impossible to get, and we don’t have networks of friends, family, and fools that have deep pockets for financing a business.  Also, there’s only a big enough pot of money in pitch competitions and business plan contests.

Having written that lamentation, I encourage you to plan, stock pile your cash, plan, and ultimately quit your job in pursuit of your venture.

(The thoughts written here are not the ideas or opinions of MIW or NSBE-BMAC but are those of your friendly neighborhood writer William Mapp.)

It wasn’t until I quit my job before gaining any real success in my enterprise.  Not having to worry about The Man gave me the time and space to focus on the important things I needed to do to build my second business, and serve our customers well.

I can give you a laundry list explaining why you should quit if you’re pursuing success. The main one being: most people can only execute on one idea really well. But, I’ll give you three quick reasons why you should quit and execute your business idea.

You’re Going to Always Piss Someone Off

I’ve Been Given Notice Several Times

Many entrepreneurs start their ventures while working perfectly fine 9-to-5 jobs.  9-to-5, the optimum hours people are available for meetings, demos, and prospecting calls. The hours many people’s minds are active and ready to make decisions.  These are also the hours you will get the most traction with pursuing customers and showing prospects your product or service. I hear you, “I’ll sneak out at lunch and set lunch meetings. I’ll meet at Starbucks and sneak back into work. I’ll go to the broom closet and make my calls.”

You’re going to piss off your manager or supervisor because you’re half paying attention, missing or unavailable, or suspiciously using company resources like computers, printers, and air. You only have so many vacation and sick days, and if you start getting a degree of success someone is going to confront you on your time commitments.

If you’re not pissing off your job’s management, you’ll antagonize your customers and make sales more difficult to get.  As cool and interesting meeting for drinks is, a lot of decision makers want to be home in the evening because they’ve been wracking their brains out during the day. Same goes for meeting during lunch, many execs and fellow business owners live high impact days if they’re operating at a high level.  Lunch and trips in the car provide times for thinking and being proactive. Also, not being available during regular daylight hours betrays a degree of unavailability when you need them most.

You’re Not Going to Be as Sharp

1+1=3, Think About It

Think about it.  You’re working a 9-t9-5, you commute (pre-covid), you decompress for a moment, and then you go to the lab to get your hustle on for your product or service.  I’ve spoken to many-a-fellow-entrepreneur who have shared stories of burn out because they were working multiple big think jobs. For many who are in tech, or working on products requiring tech, the brain strain can be intense depending on where you are in your career.

I was speaking with a woman who had started a business process automation business while working as a salesforce business analyst and she told me, “I’ve never been more busy and more worn out than I was working my job and running my business.  I couldn’t do it for long.”

You’ll make clearer pitches, write more eloquently, and build better products when you’ve given your brain the time and space to be effective.

You Need Rest

Not the Best Look

I get it.  In a COVID-19 world, we are living the life of the endless telecon and everyone books up your schedule to make themselves seem important. If you’re working two full-time efforts, something is going to slip.  As entrepreneurs we already don’t sleep, and don’t get enough rest and down time.  Lack of sleep shows up in all areas.  Your relationships with your customers, suppliers, and family members (<- you need these people) can be strained from attitude.  Forgetfulness, misspeaking, and lack of focus are all easy to notice in your day-to-day activities and if you’re working in a sensitive environment, people will notice.

And most importantly, your work product will suffer. Starting your own business and engaging in an entrepreneurial pursuit are opportunities for you to perform at a high level and deliver products and services that will not only materially benefit you, but improve your customers’ outcomes. I’ve heard stories from accountants providing services where they’ve been a million dollars off, lawyers losing the meaning of paragraphs, and software guys shipping crappy product.

Getting enough rest, makes you happy, your family happy, and your customers happy.

I get it. You want to do something different and amazing, but you’re not ready to take the plunge yet.  You want to run your business and get it off the ground, but you need security.  If that’s the case, plan, stack your chips, plan, and then leave.  But I encourage you to focus on executing one thing at a time.  You can’t scale yourself, and you’re going to need all of your wits, resources, and time to be successful in our dynamic commercial environment.

William Mapp

I am a technologist, speaker, nerd, and inventor who helps people accomplish their dreams through the use of technology. I cover stories where people, technology, and business intersect.