Entrepreneurship is certainly not for everyone, but those that want to pursue it will face challenges drastically different from those they might encounter from traditional employment. Many hurdles can show up just as you are getting started, making them all the more difficult to scale.  Preparation can help, but you have to know what to expect. So here are three early challenges entrepreneurs encounter and what you can do to better handle them.

Being your own boss

Setting your own schedule and deadlines may sound great unless you find you can’t do it. It’s one of those things that seems easy in theory but in practice requires more discipline than some anticipate. Procrastination can be poison to a entrepreneur. In my own experience, I’ve found I have to pester myself to keep working sometimes.  So I bought a digital planner app and set up checklists and reminders to keep myself on schedule. The app I used is called AweseomeNote, but there are plenty of options out there, both free and paid that can do similar tasks. In a way it acts as my virtual “boss,” even though I am the one setting the framework for it. For a newbie entrepreneur still getting used to not having a supervisor checking your progress, creating a virtual one yourself might just be the answer. It might seem annoying to have reminders chiming off all the time, especially when you just want to relax and watch a little TV, but keep in mind your future is literally on the line.

Managing your own (and possibly others) money

In many if not most cases you’re going to be responsible for taking your own taxes out of any payment you receive and entirely liable for any mistakes that are made. Add in any people you hire and you’re now responsible for tracking information they’ll eventually need for their taxes as well.  Since hiring an accountant is almost certainly cost prohibitive for someone just starting out, get some reputable accounting software and learn it well.  Keep meticulous records. This is not something you can get by with just winging it.  Sloppy finances don’t just harm your business, they can have serious legal repercussions. Assume the government isn’t going to cut you a break because you’re new.


It is easy to become flustered waiting for business to pick up, hoping a proposal gets accepted, trying to plan ahead with uncertainty of where the next paycheck is coming from. Unfortunately, there is no magic answer to solve these issues, but patience is vital to getting through them. Not everyone has the stoicism or financial stability to weather such storms, and there’s nothing wrong with that, but in order to succeed as an entrepreneur you have to be emotionally if not financially prepared for this inevitability.

These challenges are not exclusive to first time entrepreneurs of course, but your odds of dealing with them are much higher when first starting out. But by knowing they are coming and taking them seriously, you can at least be prepared to take them on as you start your new business ventures.