How to be a Successful business owner or freelancer

Perseverance. Ideas come and go. But it’s the work in the end that yields success. Keep going back to your dream that you fell in love with when you were first getting started. Keeping that dream alive will allow you to do the endless, insurmountable piles of work that stand between you and success.

How to be a Successful business owner or freelancer

Recognize that a lot of people will look at you like you’re nuts. Most of my friends went out and pursued jobs and careers straight out of college. They were taking starting salaries at $55k+ while I lived below poverty level for 2 years before getting my shit off the ground. You may have to compartmentalize or disassociate from people who do not support you. Naysayers will sap your confidence, energy and tenacity fast.


Always improve yourself as a business owner

Always be improving/polishing. Figure out how to do things better in a shorter period of time. Simple shifts in thinking can change the whole way you may perceive a problem (asshole middle-managers will call this a paradigm). If something works well, keep it and move onto the next problem. But never set anything in stone. Revamping functional code can drastically change performance. Changing the design of forms can dramatically change the choices your clients/customers make. Changing your policies can drastically cut down on returns, refunds and dissatisfied customers. Changing the way you communicate with vendors can give you back your life. Always Improve. Evolve Constantly. Never settle. This will keep you from going soft.


Get your first big success and first big failure down as quickly as possible.

If you’re just getting started. Get your first big success and first big failure down as quickly as possible. Your success will sustain you. Your failure will take off the pressure. Unless it’s an enormous fuck up of epic proportions, you’ll still be alive and able to make changes to create more successes.

But always. always. always go back to your dream. There will be times when there are nothing but obstacles. Nobody will support you. And the only thing driving you will be your dream. Keep pushing and make adjustments/improvements along the way and you’ll get there. Keep the faith when nobody else will.


Hard works pays off

A lot of hard effing work. As you grow, book keeping becomes a nightmare. Insurance, taxes, fees, permits, state taxes, city taxes, employee theft (much more than customer theft), workers comp insurance, payroll taxes, state sales taxes, quarterly taxes, state audits, federal audits, insurance audits. It’s not easy at all. It takes a lot of hard work. That being said, I make a good living after starting my business 8 years ago. It’s a pain but it’s worth it.

  • Anything you don’t know how to do well – outsource it! Focus your energy on what you do well and get HELP from others
  • Stay up to date on any legalities you’re faced with, be it taxes or making sure that your fire extinguishers are charged. Nothing kills a productive day like a visit from an unexpected bureaucrat with the ability to shut your operation down for even the slightest oversight.
  • Don’t hire your friends. Ever. Managing them is the worst thing ever. On the other side of that same coin, don’t settle on employees and hire competent people.
  • Be prepared to work your tail to the bone. Shit rolls uphill in a small business scenario. The buck stops with you.
  • Focus on making the best product / service that you can and DO NOT sell yourself short. Your time is valuable so do favors for people few and far between. Charge full price or do it for free. There should be no in between. It will set precedence for return customers to expect you to bend over backwards for little return.
  • Under-promise and over-deliver.


Running your own business gives you lots of freedom

Running your own business will not give you the freedom from the chains of work that you think it will. You’ll work more hours than you ever worked in your life. However, the quailty of your ability to chose when you work will more than make up for it. Yesterday I decided I needed to step away from my desk so I went and hit a couple buckets of golf balls with my son. I take my kids to school every day, I pick them up every day. I kiss them goodnight every night. Then, I put in the other 6 hours of work I need to get done before I hit the sack at 2AM so I can be fresh at 7AM to start it all over again. I take a nap when I need one, I eat when I am hungry. But my wife and I work constantly.


  1. As a freelancer, you are part of a global community. Look for freelancer meetup groups in your area. Or join a freelance online community. You can learn a lot from other people’s trials and errors. And you will feel motivated and encouraged listening to their success stories.


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