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9 Questions That Will Determine Your Entrepreneurial Success

Britt Robertson as Amoruso in the Netflix original series Girlboss.Karen Ballard/Netflix

The Entrepreneur Insiders network is an online community where the most thoughtful and influential people in America’s startup scene contribute answers to timely questions about entrepreneurship and careers. Today’s answer to the question, “What should budding entrepreneurs know about building a business?” is written by Cliff Johnson, co-founder and chief development officer of Vacasa.

There’s no blueprint for how to launch a business, and in entrepreneurship, things rarely go according to plan. Fortunate founders blunder their way to success, and then years down the road, step back to reflect on the wild ride. One strategy I found to be helpful when we were starting Vacasa back in 2009 was developing a state of startup self-awareness. Making time to ask the right questions in the early stages will help you shape direction and priorities over the inevitably rocky road to come.

Here are some tips to get your wheels turning:

Determine your level of influence
You’ve spent time building an operations plan, defining a target market, and thinking about how much working capital you’ll need. Now take a minute to think about what you’re willing to give up to make it all happen. Some investors are silent; others want total control. You could become an industry leader or you could hire one. Knowing the level of influence you want to retain will help drive the decisions you make.

Do you want your business to be a reflection of you, your investors, or the people you hire to run it?

Identify your best self
Once you know what you’re best at, build a career around it. For example, I’m at my best when impacting something tangible. At its heart, the vacation rental management business is about customer service and cleaning homes. I love that. I wouldn’t be a good GM of a SAAS company, for example, unless there was a meaningful connection to something tangible.

What are you doing when you hit your golden gait?

Embrace unexpected strengths
Founders have to be nimble. From customer service to board meetings, you’ll do it all, and along the way, you’re going to discover strengths you never realized you had. As an attorney, I was surprised with my business development ability. I found cold calling to be fun because closing a property is about building relationships—something I enjoy.

How will you identify and nurture surprise strengths?

See also: What Every Entrepreneur Should Be More Prepared for When It Comes to Money

Identify your weaknesses
Recognize your weaknesses early on. I’m overly optimistic, which can be a double-edged sword: Pushing too hard tends to throw off the balance of quality, efficiency, and growth.

What’s your biggest weakness?

Champion your values
How you’ll treat customers, employees, and the communities in which you operate is core to your business model. You want to get to a place where values drive decisions. If you can’t think of any values (don’t worry, you have them), create a list of words describing how you’d like future customers to feel about your service. Do it again for your employees and community.

What five words define your business?

Get uncomfortable
Being a founder is an exercise in awkwardness and poverty. Prepare by throwing yourself into uncomfortable situations. Try a new physical activity and find your limits. Push yourself to try something you’ve never done before. Do some volunteering so you appreciate how hard life can be for those who do not have as much as you do, and try to give back to the causes as often as you can through volunteering and eventually donating when your business can afford to.

What makes you uncomfortable?

Solve a difficult problem
If your business isn’t hard, it’s probably not going to be around for long because it will be easy for competitors to replicate your model. At Vacasa, we manage cleaning and maintenance operations for homeowners around the world. It’s logistically challenging. It’s also what sets us apart and what we’re most passionate about.

What’s difficult about your business?


Register for the future
It’s important to start thinking early on about where you want to register your business. There are pros and cons to having a simple or tax-advantageous structure. You might anticipate doing all your business online. Then again, you might someday want brick and mortars across the country. Make the right decision for where you want to be in the future.

How will your idea grow?

Prioritize tech
Regardless of industry, every business is a tech business. If you can’t digitize your dream, make sure to hire someone who can as early as possible.

What are your technical challenges?

Launching a business isn’t easy, but you’ll stand a better chance of succeeding if you embrace what you don’t know. Talk to founders. Ask questions. Reflect. The more startup self-awareness you develop, the better equipped you’ll be for the unexpected challenges ahead.