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Work/Life: Should I leave my salaried job to start my own business?

On this episode of Work/Life, host Greg Nibler sits down with Ciara Pressler, an author and the founder of Pregame, to ask the question hopeful entrepreneurs have been asking themselves regarding their current salaried job: “Should I stay or should I go?” When is the right time to strike out on your own as an entrepreneur? What if the job I have pays well? What questions does a potential business owner need to ask, and how do they know the right time to take that leap?

Pressler breaks down the biggest topics entrepreneurs need to consider before they strike out on their own.

• First steps: The first step, Pressler notes, is asking “What is my current money situation? What is my ‘runway’ to start this business?” Many people forget to account for extra expenses related to taxes, overhead, expenses, employees, and the other myriad costs it takes to run a business. “Be realistic about what it takes to live your current lifestyle,” Pressler says. It often takes more money than one initially thinks.

• Assessing your personal risk tolerance: While most people think entrepreneurs don’t mind tolerating large amounts of risk, Pressler notes that often may not be the case. “Figure out your own risk tolerance,” she says. If you’re not particularly fond of large risks, “you can even start your new business out as a ‘side hustle’ of your current job,” she suggests, “so you won’t be taking as much of a risk.”

• Long-term and short-term goals: As far as long-term goals, Pressler advises that you find a balance of both long-term and short-term steps. “Write a business plan for intention, but a ‘game plan’” to execute the short-term goals. Markets, industry, and businesses can wildly fluctuate, so continually updating the short-term game plan will help maintain the course toward long-term success. It might take 10 years to achieve “overnight success,” she notes.

• Who supports you?: Support structures are also an important part of planning to start a business. “Be careful when you think you can do it on your own,” she warns. “You need social capital; not just a portfolio of money, but a portfolio of people, connections, clients, and strategic partnerships” for a business to succeed. And equally important is your emotional support structure. “Who will be real with you?” Pressler asks. “That’s important.”

There’s a lot to weigh when considering going from salary to startup, “and there’s a difference between doing what you do and running a business to do what you do,” Pressler notes. But with the proper planning and a killer strategy, you can be equipped to start out the right way.

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Todd Werkhoven
Todd Werkhoven's work can be read at numerous publications and he co-authored a personal finance book called "Zombie…
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