The Fun of Coaching Frustrated Entrepreneurs

The Fun of Coaching Frustrated Entrepreneurs 7 Comments

This post was written by a guest author, if you are interested in contributing on Opportunities Planet visit the write for us page!

I started coaching small business owners, bloggers and internet marketers in 1998. I was enjoying 2 separate 6-figure residual income streams, and had a few hours a week to spare. Without much thought, I sent an email to my list of subscribers and told them I was hanging up my cyber-shingle for mentoring and coaching at $50 an hour.

Big mistake.

I was inundated. Every free hour of my life became occupied by the telephone. This was in a pre-Skype era. The autoresponder was still in it’s infancy. And I was in demand.

Before I knew what happened I was trapped like a dentist or a lawyer. I never took a day off. I even was so bold as to raise my rates a whopping 20% to $60 an hour. It didn’t matter. Back then the pioneering rush was on to mine gold on the information super highway, and if you knew your way around there was no shortage of people willing to pay you to help them.

After 17 months I called it quits, burned out and exhausted from saying the same things over and over, to the same questions, to scared people with the same fears. I shifted my time and efforts back into my 2 main businesses and quickly replaced the missing income from coaching. I vowed never to do it again.

Never, ever, say never.

Two years later I found myself in Dan Kennedy’s Platinum Club. We met 4 times a year in secret locations to discuss secret marketing stuff. And we paid through the nose happily, just for the privilage.

It’s mind-expanding to be a mid-six figure earner in a room of seven figure earners. I was astonished to see how these entrepreneurs almost invariably had a high priced mentoring and coaching program for their top clients. That year I learned so much from hanging around with big thinkers that my expectations were permanently stretched. With some trepidation I made a new plan and took a deep, deep lungful of air and made a decision.

I relaunched my personal coaching program in 2002 at $500 an hour. In my industry it was unheard of. Within a month I had a waiting list a month long just from my in-house database of 83,000 newsletter readers. And my personal ambition got me, again. Within a year I was coaching 30+ hours a week. Plus group classes. Plus live seminars.  I had never made so much money in my life just from helping other people to succeed.

My competitors criticized me brutally for having the highest price point in my niche. But it was astonishing to see the calibre of individual that you attract when you simply charge the top dollar.

The real fun came from seeing my clients get results. I realized that helping the ambitious to remove obstacles, stretch, reach and overcome was a major reward in my life. After a decade of working with entrepreneurs I have a pretty clear idea of why we do what we do, our common sticking points and some simple strategies that produce incredible results.

Check this out.

When I was charging $50 an hour, my clients would often love the input, and then do nothing with it. That was frustrating.

When I raised my fees to $500 an hour, my clients would often love the input, and then still do nothing with it. Which was suprising but a little less frustrating!

Here are 4 things I do with every client within the first month of working with them.

1. Daily Inbox Zero

My goal is to equip the client using 2 main tools to run their life. One is Evernote, and the second is Gmail. Both work on iPhones, Androids, PCs and Macs. Being cloud driven and app specific rather than device specific reduces the friction in their life.  No more suffering while chained to a desk, and no more lugging a heavy laptop on a plane.  Stress is reduced with the confidence to run your empire from any device with internet access anywhere in the world.

Every morning at 7:45 am the gmail inbox is emptied to zero emails. This takes less than 10 minutes in nearly every case. If an email demands an action, it is forwarded directly into a folder in Evernote called Daily Activities. The client works from the Evernote box not the Gmail inbox. If the client’s life is email heavy, then they check it again at 4:15 pm. In almost all of my clients this has been more than enough. (most are solopreneurs, creative types or freelancers)

Email overwhelm is a disease for entrepreneurs. Eliminating it through a systemitized process is a top priority.  Business owners make the most money by thinking, not by reacting to email.

2. CRM Replaced by Gmail

For a decade clients and I have struggled with tools to manage the people in our world. From brutual overkill solutions in the cloud to open source to platform solutions to paper and pen, nothing ever seemed to work as elegantly as it should.  I remember “fondly” being chained to Outlook on my PC that chugged helplessly under the load of the horrible programming.

Today I use Google Gmail with a free plugin called Rapportive, as do many of my clients who aren’t trapped in legacy systems or part of a dinosaur corporate bureaucracy.

With advances in cellular technology and the cloud, there doesn’t seem to be a more streamlined and frictionless environment for tracking relationships. What good is a super system if you never use it?  The busier the entrepreneur, the more important simplicity becomes.

The in-box is what I refer to as the Kirk Position. Remember Captain Kirk on the bridge of the Starship Enterprise? You have the most influence and trust with people through their inbox, not through Facebook, Twitter or a webpage.  Striving to control the clients in-box and increasing the depth of the communication with people through their sacred space is a high value activity.

3. Rituals Defined And Protected

It’s astonishing how poorly some of the top earners in my universe treat themselves. The classic overachiever pushing to the max on scotch and cigars and sugar is destined to be a short-lived player in the game. I work dilligently with clients to develop, define and implement strategic rituals in their life.

The hour before bed is a big one. Something as mundane as filling the coffee maker the night before instead of sleepily doing it while rushed in the morning can have an impact on productivity.

I used to be guilty of checking email and social media as the last thing before sleep. Never again. Now the process is to unplug from the matrix at least an hour before eyes shut. That includes tv, Angry Birds, the iPad, and obviously soda and coffee. The reading of ficition while in bed creates a relaxed breathing pattern that signals the brain to wind down. Try 20-30 minutes of Terry Prachett and see if it changes your sleep experience!

Experimental sleep-inducing meditation makes a profound difference in two thirds of my clients. Visualizing a strong lock box and putting their fears, worries and anxieties in it for tomorrow is step 1. I have them turn out the lights and put their minds into the space in their toe joints. Their awareness slowly goes up each joint in the ankle, leg and hips feeling the space in between each joints. Breathing is in and out through the nose with the belly expanding. As consciousness fades away they implant a single command as a finally memory. Dream good dreams.

The morning rituals are extremely important. After 14 years of waking at 8 am I reprogrammed my personal wake up time to 5:55 am. I make a cup of coffee, feed the cat, then write in my journal for 45 minutes. I eat a protein bar, grab a second cup of coffee and write a blog post until 7:45 am. I then empty my email, dump the action items into my Evernote action folder, and make a cup of mint tea and sit by the fire with my wife for 45 minutes. By 9 am I am back in the home office for 2 more 45 minute sessions of either writing or coaching. At 11 am I do my yoga session, then have lunch with my wife. Then I put on my light and sound machine and do a 45 minute holosonic meditation session. The remainder of the day is free to spend with my family.

4. Determine The Smallest Unit of Work Possible

Even the most ambitious and productive of us have off days. Every entrepreneur possesses at least some idea of what their own smallest piece of work that still provides the ego satisafaction of a completion is.

What do I mean?

If you are a blogger, is your smallest unit of work a 500 word post? Or a 300 word post? Or is it simply the creation of a juicy post idea on an index card?

If you are an information marketer, is it writing an ebook, a page of an ebook, or writing an ad to post on Elance to find an outsourcer to write the ebook for you?

Sometimes the smallest unit of work is just that. You do it, you feel good, and call it a day. Sometimes when you do the smallest unit of work it creates a small burst of momentum and some real stuff gets done. The key lies in having a personal clearly defined rule surrounding the smallest unit of work.

I aspire to be my own best coaching client. In my mid-forties I am in better shape and more productive than in my mid-twenties. The 3 books I wrote and self-published in Amazon this year are a reminder of how much you can get done when you have a plan and execute that plan.

The technologies that my clients and I have used have dramatically changed over the decade as you might expect. But the basic routines that form the foundation of extreme productivity haven’t changed since the times of Benjamin Franklin.

Keep these in mind:

  • Wake up early
  • Keep the main thing the main thing
  • Block distractions
  • Sleep good
  • Enjoy the ride

After being an entrepreneur for over two decades, and a high priced coach for 13 years, I can tell you those 5 things can help a frustrated entrepreneur with 90% of the stress in their life.

The good news?

You’re the boss.

The bad news?

You’re the boss.

Embrace your freedom as a business owner.   Good luck in your business!

This post was written by a guest author, if you are interested in contributing on Opportunities Planet visit the write for us page!


  1. For me the number one cause for me is stress because If you are stress in your work one day your are not in condition and your body going down..

  2. So true Fatima. Weak body = weak production. That’s what concerns me about the future crop of kids coming up as entrepreneurs. Morbid obesity with limited education is a dangerous combination.

    What are you working on that’s interesting?

  3. I’m fascinated by the gmail to evernote in box tip. I’ve gone back and forth on evernote, just never loved it. But I CAN NOT STAND having mail sitting in my inbox. I’ll definitely check this one out! Thanks for this tip.

  4. I have been using gmail for 7 months now and it is fantastic, i should have switched ages ago.I will also be trying evernote because i struggle with getting organised where emails are concerned.


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