The 20 Hardest Things About Starting a Business


People often say that if you make it five years in business, you’ve beat the odds. What they don’t often share with you are the things that happen in those first five years that contribute to the high number of people whose businesses don’t make it.

I’m here to tell you about the personal hardships you’re likely to face in the early stage of business ownership. If someone had told me about these, I might have saved some tears, prevented an early wrinkle and lowered my blood pressure. These tips are straight from my personal experiences starting various companies in the past several years:

  1. It’s lonely. Whether or not you have a partner, it can be lonely. Your hours will become nontraditional, you may be working out of your home or in a small office, and you will focus all your attention on work. None of these factors make for a great social life early on. Realize that this stage is temporary and try to make time for people who have been there before. They can demonstrate that it gets better and help you take your mind off work.
  2. Business partnerships are hard. Just because you are “best friends” or have “opposite skill sets” doesn’t mean you’ll make ideal business partners. (I work with my twin brother, which needs its own guide book!) At the end of the day, treat a business partnership with the respect you’d give a romantic partnership. Also consider a “pre-nup.” This should be an operating agreement (get a life insurance policy too so you can buy each other out if a fatality occurs). Above all, be cautious before you commit to a business partner. You don’t want to take valuable time, energy and money away from the business to break up your partnership later.
  3. You will be poor for a while. Unless you have a trust fund, a huge savings account, or a wealthy partner, chances are high that you’ll be scraping by for a while. In the long run, this will help you make savvy financial decisions. But while you’re in it, it won’t be easy. Every decision begins to look like it’s colored by a financial lens. You’ll realize that you might not be able to go to dinner with your friends, take vacations or go shopping. You may even cancel your gym membership and magazine subscriptions (I did). This is all a great training ground for when you do have money — hopefully you’ll remember these tough times and be careful with your earnings.
  4. It’s way less sexy than you think it is. We see a lot of images of cool entrepreneurs who made it big. Most of these business celebrities went through hard times but don’t get the opportunity to talk about them in the media, can’t remember them well, or don’t want us to know about the hurdles they jumped. This is like the entrepreneurship version of airbrushing: It looks great on paper, but deep down, you know it’s fabricated.
  5. You will doubt your abilities. Your business will challenge you. You’ll face forks in the road you could have never predicted. When you lose your first (or 10th) big client, your employees quit, you divorce your partner, your balance sheet looks dismal, or you can’t get financing, you will likely start to doubt yourself. Dig deep to get through these times. Ultimately, you need to be your biggest cheerleader.
  6. You will think you are the only person who has gone through this. Let me be the first to assure you, many have been through this before. Many have failed. Hopefully they got back up and tried again with something new. Many have succeeded, too. None of it matters if you don’t work hard for it, so keep moving forward and find someone who’s more seasoned in business to mentor you.
  7. You will cry. People often compare their business to children. When your baby has a good day or a bad day, you might find yourself crying. It’s OK. Feel it and move on.
  8. You will never know what to expect. Think of the life of your business like the stock market. There will be ups and downs, but hopefully it will make a positive upward trajectory over time. Address the issues, make a plan and execute. We are defined more by how we got up after issues arise than by how we scoot through the easy times. Napoleon Hill once said, “Most great people have attained their greatest success just one step beyond their greatest failure.” Don’t be afraid to take that next step.
  9. Mistakes are inevitable. If you fear mistakes, you’ll never make progress. Do your best to trust your instincts, ask for guidance from trusted sources when you need it and keep moving. Don’t make the mistake of inactivity.
  10. You will feel clueless at times. It’s impossible to know everything about running your business. When you have legal, accounting, IT, real estate or other inevitable questions, get referrals to trusted experts from people in your network.
  11. Don’t compare yourself. It’s natural to want to benchmark your success against peer businesses. Be wary of doing this. Regardless of how successful they are or are not, be the best you can be and don’t waste energy comparing.
  12. It may not work at all. There is a strong possibility that your business may fail. This is simply a statistical reality. If you’re not afraid of failing, keep going. If you are, you may want to reconsider self-employment.
  13. Fancy words just cover up real issues. People tend to make up trendy words to cover up inevitable problems. If you are facing an issue, pivot. It’s always good to have a positive attitude. But don’t let people’s ability to gloss over issues make you feel down because you don’t use fancy words to cover up yours.
  14.  You will be afraid of not being able to pay your bills (business and personal). Ever felt fearful that you’d miss payroll — or your rent? So have the rest of us. As long as you’re making wise financial decisions in line with your projections and current revenues, you have to push these fears aside and keep selling (or fundraising). That’s the only way to pay those bills, after all.
  15. Your family and friends may question or doubt you. I’d be lying if I said I never got a call from a close friend or family member who “lovingly” asked me if I was sure I was doing the right thing. If you aren’t strong enough to believe in yourself and your ideas when these constructive criticisms come your way, it may be time to consider your choice.
  16. You won’t work from 9 to 5 anymore. If you’re seeking freedom of time by working for yourself, that won’t likely be the case in the early stages. When your friends get off work before dinner, be prepared to work into the wee hours when necessary.
  17. Say sayonara to a good night’s sleep. You’ll be thinking about the business all the time. It will cut into your sleep, relaxation and time with friends and loved ones. I like to send myself emails or write notes on my nightstand so I can try to get the maelstrom of thoughts out of my brain and get some needed sleep.
  18. If you build it, they might not come. This is the cardinal sin of retailers and e-commerce stores who create a storefront and expect people to just walk in the door or find their site. You have to have a marketing plan in place. Execute it daily to be sure customers are finding you.
  19. You can’t have black without white. Without bad, it’s tough to appreciate good. Take the hard moments and remember them in the good moments. It helps to give you perspective and be grateful for successes, big and small.
  20. There is no such thing as overnight success. No matter how you frame it, it takes years of hard work to become an “overnight success.” Just because someone’s business is a couple years old and gets sold for a billion dollars doesn’t mean it was an easy path.

If this doesn’t scare you, congratulations: You’re likely meant to be an entrepreneur. Just remember to pay it forward to other entrepreneurs and share your stories with them, too.

Darrah Brustein is the co-founder of Equitable Payments, a merchant services brokerage, and founder of Network Under 40, a monthly networking event for young professionals. Darrah authored Finance Whiz Kids, a series of kids book that teach the basics of financial education.

The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world's most promising young entrepreneurs. In partnership with Citi, YEC recently launched StartupCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.