How to Survive the First Year of Entrepreneurship

Yuriko Simpson, left, and Miles Simpson prepare a to-go box for a customer at the 2 Jerks stand during the Camp Foster Festival in Okinawa, Japan. The stand is run by retired Staff Sgt. Fredrick I. Simpson. Simpson’s family helps him serve food and drinks during festivals across the island. (U.S Marine Corps/Lance Cpl. Tayler P. Schwamb)

Much like marriage, medical school and a stringent diet, the first year of entrepreneurship is often the most challenging. You're filled with excitement, fear, questions, confidence and drive. And perhaps similar to your first year in the military, you wonder whether you're cut out for what this entails.

Starting your own business can take many forms: You might purchase a franchise, where many of the systems and processes are documented and ready for you to launch. You may have created a technical solution to a business challenge and have a unique offer to a very specific target market. Maybe you're starting a business with a physical storefront. Or perhaps you're launching a new career in professional services, offering consulting, coaching, legal or financial advice. 

Whatever type of business you're starting, getting the company structured, launched and then doing the work of the business takes up much of the first year.

First-Year Entrepreneurship Tactics

Depending on the nature of your business, you will face several procedural tasks that require preparation and attention, including: 

  • Deciding whether you need a business plan (investors will likely require this). If so, who will write it?
  • Setting up your financials: How will you invoice? Which bank accounts will you need?
  • Deciding on investment structure and documentation: Will you gather outside investments?
  • Which business structure is most fitting? How will you file the business with the secretary of state? Will you be an S Corp? B Corp? LLC? Other?
  • What financial and business assistance is available to you because of your military service?
  • How much insurance (and what type) will your business require?
  • Will you purchase or lease equipment? How will those get financed?
  • How will you handle human resources? Will you hire employees or independent contractors?
  • Deciding on branding. What is your business' value proposition and offer to the market?
  • What marketing will you need in Year 1? Will you need a website, business cards, social-media profiles, etc.? Who will manage those?
  • What other tasks (specific to your business) need to be completed now?

You may not be an expert in all aspects of finance, legal, marketing and human resources areas needed to get set up, so consider engaging professionals. A good CPA (with specialty in your business area), lawyer, HR professional and branding/marketing person is a smart investment to be sure you're set up for success.

Retired Staff Sgt. Fredrick I. Simpson, left, and Jamie Gibson grill at the 2 Jerks stand during the Camp Foster Festival in Okinawa, Japan. (Lance Cpl. Tayler P. Schwamb/U.S. Marine Corps photo)
Retired Staff Sgt. Fredrick I. Simpson, left, and Jamie Gibson grill at the 2 Jerks stand during the Camp Foster Festival in Okinawa, Japan. (Lance Cpl. Tayler P. Schwamb/U.S. Marine Corps photo)

First-Year Entrepreneurship Feelings

Not to be overlooked are the slew of emotions you'll experience during the first year. You might feel any or all of the following:

  • Why is this so hard? I thought it would be more fun.
  • I'm finally doing what I love! This is awesome!
  • I need more help. I feel overwhelmed. Where can I find help to get over this hurdle?
  • I'm struggling to bring in new business while doing all this work. What am I doing wrong?
  • Business was great for a while, but feels like everything slowed. I'm trying not to panic.
  • I hired the wrong person. I hate that I must let them go.
  • I'm feeling so much more confident in what I'm offering.

During the first year of my business, everything felt hard and exciting at the same time. While I'd worked in the business world for 20 years, I'd never started a company from the ground up. I leaned on a lot of people for advice, support, guidance and mentorship.

Surround yourself with people who'll support and encourage you this first year. Your family and friends can give you emotional support because they know and believe in you. Find mentors who've built companies, especially in your industry or field. Seek mentors who were also prior military members, as they'll understand your experiences differently. And lean on people who're offering their guidance to help you succeed. You don't need to do this alone.

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