I am a serial entrepreneur seeking personal freedom within one year. This site is about that journey.

Cookie Carts and Business Strategy Part 1 (Intro)

I had a friend named Evan who always used to say… “What happens if the cookie cart runs over you?”

Is that a bad thing?

Is that a bad thing?

It always got me thinking about how to continually look for ways to remove myself from my business. That sounds lazy… but it’s actually a LOT of work, especially in the beginning! Consider for a minute what would happen if you were to leave your business for a day. What about a week? A month? I would guess that most small businesses would not be able to survive without imploding much beyond a month without the owner at the helm. If you are like me, being self employed… there really is no such thing as a ‘sick day’. Sure, we have all sorts of flexibility with our schedules… until someone sets something on fire.

It's going to be one of those days.

It’s going to be one of those days.

Quite honestly, it can sometimes feel as though you are always working in the triage of an emergency room. If you are in a business that charges a premium for ’emergency room’ type services, that might be great … but most of us never thought that we would be in that type of business until years later and we find that all of our time is consumed with setting bones and plugging bullet wounds. The worst is when you are the only doctor on call with no-one else to turn to for help. Most of us dreamed of getting paid top dollar for expensive surgeries in a well structured operating room, not pulling marbles out of a toddler’s nose.

I learned it from you, dad!

I learned it from you, dad!

In this series, I’m going to teach you some of the methods that I have used to keep things moving forward in my business even when I’m not around. Your mileage may vary, and even though I’m going to try and keep it fairly generic, some of it might not apply to your business.

As always… please feel free to comment and let me know your thoughts! I would love to learn what you are doing!


Continue reading this series here!
Cookie Carts and Business Strategy Part 2 (Mindset)






Finding Freelance or ‘Work From Home’ Jobs

If you are fortunate enough to be in an industry that allows for it, there are many opportunities to be found online to work from home. Most of the sites built for freelancing have a strong focus on IT related work, but several of them cover many other soft-touch areas such as writing, marketing, sales, telemarketing, virtual assistance, graphic design, etc… I’ve tried several of them and have had success with some:



Being self employed, ODesk has always been my favorite freelancer type site. I have worked with them as both a service buyer and provider. They have a great system for keeping track of time spent on various projects, an awesome user profile and review system, a very large community of users. Their policies are straightforward and common sense. Their fees are also reasonable. They have a great timekeeper application that eliminates the need to manage time spent on tasks, or you can enter your time manually. They also support fixed price projects. As an employer, Odesk is super easy and straight forward. Employers pay nothing to use Odesk or post a job.



Elance is now merging with ODesk, which I think is great for both communities. I’ve always considered them to be pretty expensive if you really want to make best use of them, but they have recently made some significant changes to their fee structure, opting for a flat 8.75% model similar to Odesk.






Another contender in the freelancing space, these guys have a really vibrant community of freelancers and employers. Their fees average between 7% and 12% depending on several factors.


Everyone loves to trash Craigslist, but I have actually had some success finding freelance gigs there. Use street-smart common sense, and you will too. When in the jobs category, do a search for ‘telecommute’ and / or ‘contract’. Also don’t be afraid to contact job posters and ask them directly if they are open to telecommute. You may be surprised!



Probably one of my least favorite freelancer type sites. Freelancer.com users are extremely competitive, and as a domestic software developer I have had very little luck with getting jobs there. Estimated budgets are frequently set way below where they should be, and buyers will infrequently give complete information for a bid requiring estimates. The fees they charge are also high in my opinion, on a sliding scale based on the membership that you choose, anywhere between 3% and 10% of the job. They also charge employers another 3%. As an employer, they have fees out the wazoo, pretty much following the Ebay model. Their website has also been very buggy lately, and doesn’t even really work well at all in Chrome. They do have escrow built in though, which is nice.


How do you find freelance / work from home jobs? Let me know in comments!

Why I need a job, and you do too.

This may very well wind up being the most ironic post I make to this site as a serial entrepreneur who has a goal of personal freedom. After nearly a decade of self employment, I have once again come to the conclusion that I need a job. You see, this isn’t the first time that I’ve realized this. Oh no. I have shared several times in the panic and anxiety that entrepreneurs collectively call ‘feast or famine’.


This kid gets it.

In the past, each time that I have come to this conclusion… I have always viewed getting a job as the worst thing ever, and only reluctantly and as a last resort would I pick up something full time for a short period and fly like the wind as soon as business picked up again for my own gig.


This is the stuff that dreams are made of.

As a self employed entrepreneur, I am responsible for … well… everything. Not only do I need to come up with the money every month for my own mortgage or rent, electricity, phone bill, food for my family and pets, car expenses, clothing, insurance, doctor bills… everything that it takes just to live, but I am also responsible for paying my contractors, my hosting bills, software licenses, business insurance, accounting, taxes, telephone bills, hardware / computer expenses, bookkeeping, everything that is needed for my business to survive. Not to mention all the time that it takes to deal with all that stuff if you are the only one doing any of it.

I can’t count the number of times that our personal savings has gotten wiped out in order to pay for business expenses during lean times. It gets pretty tiring.

The last time I struck out on my own, it was after getting laid off back in 2009. Nearly 5 years later, I am realizing that I did not have enough of a platform to launch from at that point. You see… because I started my business from a weak foundation, I have not been able to say no to any paying work. Don’t misunderstand me, I am not ungrateful. Quite the opposite! I am so very thankful that I have had the opportunity to serve my clients! However, there has been a lot of work over the years that I have taken on that did not always fit the vision for where I wanted my fledgling company to go, and as a result of this, I have not had the freedom to really be able to steer the ship and instead have allowed it to be carried along with the current of whatever brought cash in the door. The pressure to say ‘yes’ to everything is enormous, and it can hinder your ability to negotiate agreements or even request payment from your clients when they fall behind.

He has no problem saying no.

He has no problem saying no.

So… I’m going to try something different this time. I’m going to get a job and keep it, and I’m going to focus on building a business and systems that don’t require me to work full time unless I want to. This is, after all what my end goal for personal freedom will require anyhow, right? What do you think?

What is personal freedom?

The most appropriate (for this site) definition of  ‘Freedom’ from Websters is:

1: the quality or state of being free: as

a : the absence of necessity, coercion, or constraint in choice or action

Personal freedom on the other hand is well, Personal. Everyone has their own idea of what freedom really means to them, and so I have defined it for myself in these ways:

1) The ability to manage my own time in a way that gives me the choice of who I want to spend it with, when, where, and how I spend it.

2) The ability to choose not to work for a living, but to instead work because I want to.

3) The resources to choose to give of my time and money the way that I wish.

For me, one way for me to measure this is by measuring my passive income compared to my expenses. I’ll be reporting these figures regularly on this site.

The goal of this site is to allow me to further explore during this year what personal freedom really is for myself and my family, and to hopefully find my way to it by the end. It is my sincere hope that along the way I am able to help others to find for themselves what it really means to them to be personally free, and maybe join me in my quest. My plan is to post regularly about those things that I have found helpful as I progress in my journey to a life of freedom. 🙂 It is sure to be an interesting and hopefully enlightening ride.

Feel free to leave comments about what Personal Freedom really means to you!