These difficulties probably apply to most small businesses in the USA. Look for a follow-up post on the positive flipside.

I’ve been in the entrepreneurship game for almost 7 years now. I enjoy the unique lifestyle it has formed. If the following 3 hard things weren’t in the mix, or the pain was lessened, I would say entrepreneurship is fabulous.

Health Insurance Costs

I’m refraining from making this a political commentary but let’s just say I agree with Ringo Starr, “Everything government touches turns to crap.”

Our health insurance costs have skyrocketed over the years. Now we pay over $1100/month for a family of 3. This isn’t a negotiable expense and I can’t optimize it. And it is supposed to keep going up…

We do have a “medically demanding” child so I am grateful for insurance. However, we’re at a point where if we just paid cash for all our meds, surgeries, and specialist appointments it would be less money than we spend on insurance!

Tax Rate and Burden

It’s a discipline and cash flow problem as much as the heavy burden of the amount.

Making quarterly payments can be really hard when you’re trying to scale a business and make investments in growth. If you’re a prudent risk-taker you’ll likely purchase software that makes you more efficient or lets you scale in the short-term rather than send that same money to the government. This can burn you.

As a small business you’re in a terribly awkward position of paying a far greater actual rate than an employed individual or a larger corporation.

Cash Flow Unpredictability

This is an issue more particular to a Web Services Firms. You’re usually in feast or famine mode. It’s a tough way to live.

This has become less of an issue with retainers and providing Hosting & Caretaking plans. But it is still tricky and compounded by the first two difficulties above.

Would I Recommend Entrepreneurship?

I’ve really wrestled with this question over the years.

It surely isn’t for everyone. You (and your spouse) need a strong constitution.

In the current state of things I would recommend someone run a “traditional” employment course for a few years and make mistakes on someone else’s dime. Save up enough to live on for 6-12 months, and then start to ease into an entrepreneurial lifestyle.

Those are my thoughts, would love to hear for you. Comment below and let me know if there are other difficulties you face and if you would recommend entrepreneurship.