Winter comes every year. It’s no surprise for most people, except usually entrepreneurs….


The biggest fear anybody I’ve ever met has when it comes to being an entrepreneur is losing that “steady and reliable” paycheck, the employer’s version of your childhood blanket. I always try and let them know after some time you will think about money in a different way and learn to budget accordingly but it’s still a shock to their system and probably the biggest mental roadblock out there for budding self-employed people.


I spoke to a local friend earlier this year who is TREMENDOUSLY successful at his current job, he will easily earn 400k in 2018 as an employee – impressive right?




How is that not impressive? He would have made around 1.2M had he done the same thing performance wise for himself. Sure there would have been expenses but we went through them and in general that only brings the total down to around 1.05M. Most of what he does is performance based and in that business it’s very clear if your performance is related to your experience/drive or that of those around you. It’s just not really a “team sport” type of venture. Why isn’t he already on his own? That comfort blanket, even though in his case it’s a drop in the bucket – is still there. That and he knows through experience (see 2008 economic implosion) that winter is coming. But this guy is strong, and he will get there. Frankly, even if he doesn’t the worst case scenario for him is he will be less rich, but still very wealthy. So in a way this is a rare case of win/win regardless. But…..


Would you trade 400k for 1.05M? OF COURSE YOU WOULD.


NO. I’m not saying 2008 is going to occur again anytime soon, but we will hands down face another recession at some point – that is just a face of the American (or any) economy. The US, in particular, can be described over the long run as “BOOM, BUST, BOOM” in a repetitive fashion. For those with strong/stable goverment jobs this probably doesn’t change your planning, especially if your employment is in the categories where even federal/state budget cuts are unlikely to touch (essential services). If you are in the private sector thought of another recession probably looms large as many were completely out of work for some time, years in extreme cases. That is the beauty of self-employment in many cases – your business may be down, but if you have multiple clients (and you should) then zero won’t be seen – even in something like the great recession.


So where am I going with this rant? Your own personal safety blanket.


Maybe a little extreme. But you get the point right?


For the self-employed carrying minimal personal debt and a solid cash/cash equivalent position will eventually take the place of your employer’s safety blanket paycheck and you will feel better about it. Make no mistake, no matter what industry you are in with few exceptions winter is coming. Sales will get slow. Clients will leave. Costs will go up. Life will happen and prevent you from fully focusing on your ventures. WINTER is coming, so be smart about your life before it gets there and stockpile what you need. Man has been doing this for the longest time, it’s ingrained in your DNA to prepare for winter – it just isn’t taught to do so with your personal finances as well. The smarter you are with money the easier it will be to control your life and pursue the ultimate true freedom of self-employment.


After all, it’s important to point out that roughly 70% of employees in the US work for another small business. Those companies don’t make payroll through magic, they do it the same way you would if you were self employed – good planning.


Just because you don’t know the fact that there were many times your boss played Russian roulette with getting your paycheck cleared doesn’t mean that it didn’t happen. So before you cancel out the idea of entrepreneurship because of a silly safety blanket try getting ready for any winter that may come your way BEFORE making the leap. You will operate differently, more freely, and I will wager be a better businessman because of it.



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