Having been an entrepreneur for over 30 years, a young man asked me to comment on What Keeps Entrepreneurs awake at night.  That question resonated deep within me.

On many nights, a fine scotch put me to sleep when faced with what appeared to be insurmountable problems each of us faces.

The primary thing that I have learned over the years is that we fail to leave the Technician role we start out with according to Michael Gerber, author of the E-Myth. Gerber says there are 3 people in the head of each entrepreneur, the Technician, the Manager and the Entrepreneur. There exists a distinct difference as each of us grows through those roles and levels in our businesses.

Once an entrepreneur can give away control of doing the work, of the technician, and move onto the manager role the stress will diminish and that increasing workload will take a different turn. Now your goal is to keep your new employees busy and get out of your head that confused notion that you gave away control, that only you can do the job right.

I asked a client when he thought he might be over the ‘hump’ in his business. He thought for a minute and said that in year five he thinks he will be able to take a week holiday to his home country with his wife. He didn’t get the concept of Technician.

Organization will give you a good night’s sleep. Planning on a regular basis and time management seems to elude the average business person. I used to get up in the middle of the night with worry and run to my computer to jot done some ideas, ahghg.  It took me years to understand the basic concept of time management and planning.  It also doesn’t help a marriage, or two.

Financial planning, or lack of specifically, is critical. In the old days, working from home was a no-no; it made you look like and amateur. In keeping with that theory of course I had a huge 5000 foot office in downtown Vancouver. Imagine trying to come up with that overhead each month; high-speed T1 line $3000 and rent $5000 plus, plus, plus. Now everyone has a home office if possible.

Having enough operating capital is always a problem it seems when I talk to clients. There’s never enough planning in how much money an entrepreneur needs to setup their business primarily because no one considers doing a startup budget. Seems logical to me to have one.

Prepaying the pain is my favorite concept that keeps us awake at night. I remember doing a job for a client and had made my invoice. With a high 5 figure invoice I was aghast that my client would be upset and question my billing. I ignored my client’s calls for a week and could not sleep with worry. I finally made an appointment on Friday for Monday to present my bill. I didn’t sleep all weekend. On Monday I pulled my courage up, gave the CEO my invoice and waited for a harangue. He thanks me for a job well done and wrote a check for $75,000. We went on to do a lot business together, yikes! I had suffered for nothing. – My new mantra? Doubt Kills the Warrior.

Deadlines? I’ve come to observe that contracts, deadlines and schedules have to be guidelines. I’ve sweated over performance based deadlines many times. Once I explained the scenario to waiting clients it was easier to reevaluate and renegotiate timelines than to have a heart attack over missing one.

It all comes down to planning, financial management and understanding that you don’t have to run your business all by yourself!

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