Considering Starting a Business? Here’s What That’s Like

The most challenging aspects of entrepreneurship and how successful business owners overcame them.

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Successful businesswoman with an e-business working from an office at home telemarketing and taking orders over the phone or consulting with clients, high angle view
Successful businesswoman with an e-business working from an office at home telemarketing and taking orders over the phone or consulting with clients, high angle view

Deciding to start a business is a big deal and given the state of our current world, it’s both scary (hello financial insecurity!) and at the same time, precisely the opportunity some closeted entrepreneurs needed to finally take the bull by the horns and do it.

However, as an entrepreneur myself I can tell you: this is not for the faint of heart. Yes, there are some AMAZING aspects of running your own business like setting your schedule to best suit your life, unlimited vacation days and no micromanaging!

For me, it’s been one of the best decisions I ever made.

There are also some scary realities that COVID19 has brought even further into the spotlight. (Think: payroll, health insurance, how to survive if/when government forces you to temporarily close… and the list goes on. )

Challenges When Starting Out

When I first started DCM Communications, the pressure to sell became the most taxing aspect of being an entrepreneur, which was ironic given that I had trained sales people on more effective methods when I worked in the corporate world. I used to teach them how their confidence immediately ties to sales and knowing when to walk away. Yet when it came to selling the ideas in my brain as a consultant, the game got harder.

My internal dialog went from “I’m offering a solution to a specific problem” to “Oh man I need to get this client at whatever cost to me because I need to pay my mortgage!” 

For Melissa Park, New York-based global event producer, the need to find her tribe topped the list. “There is so much about entrepreneurship that can be a challenge, but feeling like you are doing it alone is definitely at the top of my list.”

That solo feeling extends to the decision making too. Amaia Stecker, managing partner at Pilar & Co in Alexandria, echoed the sentiment. “Even the best paid consultants can only offer advice; you have to make all of the decisions. That’s a big weight to carry.”

Overcoming These Challenges

Despite these first challenges, entrepreneurship does not have to be a lonely, confidence-shaking journey. The key is asking for help.

Personally I turned to a business coach to give me the best foundation possible so I could (hopefully) avoid some of the common pitfalls small businesses encounter when starting out. Add to that some amazing clients who saw fantastic results from our work together, some less-than-amazing clients who showed me what I do NOT want to do again, and my confidence in the ideas in my brain came back.

Stecker chose to outsource aspects of her business so she can focus on what she loves and does best: event planning. “Associations don’t hire me to do their books. They hire me to plan effective and meaningful events that further their mission, so I focus on that and let my accountant manage the P&L for my business.”

Park turned to collaboration hubs and community groups in New York to find likeminded entrepreneurs who could both offer guidance and support when she needed it.

“I joined Luminary (a collaboration hub) here in New York and its’ fantastic! I’m able to share a co-working space with other women entrepreneurs so we get the sense of community even though we each have our own businesses to work on.”

Despite our differing challenges, we all agree that entrepreneurship is not for the faint of heart. Each of us has chosen not to hire full time staff but rather utilize contractors where needed to deliver the best results to our clients.

That is not a realistic option for all business models, some of which require full time staff. The key to getting it right and not just surviving as an entrepreneur, but thriving, is knowing when to ask for help and turn to experts in their respective fields to guide or work with you to build a business.

If you’re confident in your service offering and vulnerable enough to know when to bring in outside assistance, then entrepreneurship can be the best decision you will ever make.

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