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The 5 Smartest Things I Did My First Year as an Entrepreneur

Advice for people who want to start their own businesses

By Jessica Thiefels

(This article was originally published on Next Avenue in 2017.)

Running a Business
Credit: Adobe Stock

As a 28-year-old, my experience as an entrepreneur may not be the same as if you're getting a business off the ground in your 50s or 60s. Still, if you're hoping to launch a full-time or part-time business in midlife, it’s likely that many of my struggles would mirror yours. That's why I think you can profit by knowing the lessons I learned in my first year running my business as a physical trainer.

I’m sharing my experience in hopes that you’ll find ideas, inspiration and even solace in knowing that you have company in this exhilarating and challenging madness. Here are the five smartest things I did in Year One:

Smart Thing No. 1: I Took Nike’s Advice

As you get closer to starting your business, you might be thinking: “I’m not ready yet!” While there are some cases where you truly need to get all your ducks in a row before launching, most of the time your best bet is to jump in.

This was a tip from one of my mentors. I asked his advice about how to start as a personal trainer, and he simply said, a la Nike: “Just do it. Just get started and see what you learn; see what happens.”

Without that advice, I likely would have waited another six months to start and wouldn’t be where I am now.

I’ve used the “Just do it” mindset in many areas of the business in the past year as well. When I have an idea, I often remind myself to just try it rather than hemming and hawing over the details. For example, I wanted to test Facebook Live as a way to attract clients. Instead of spending weeks planning how to do this, I just did it. While this particular idea has yet to pan out as a valuable tool for me (more on that shortly), I did learn how the platform works and was able to experiment, which was valuable in itself.

Smart Thing No. 2: I Created a Support System

As a first-time business owner, you’ll have tons of questions, from operations to finances. On top of that, you can get burned out from non-stop thinking, working and planning. Having a support network to help answer those questions and guide you along the way is critical.

While I’ve known some people in my business’ support network for years, others I had to seek out by networking or going for coffee. This process can be tiring, but as Ted Rollins, global entrepreneur and co-chairman of Valeo Groupe says, the payoff is worth it: “Finding people who challenge your ideas, push you to be better, and give you developmental feedback — the trifecta for success and growth —requires hard work. Find events, networking and otherwise, where you can connect with people that cross geographical, organizational and hierarchical lines, and you’ll be on your way to success.”

Instead of looking at building my support network as a chore, I tried to think of it as a fun way to uncover ideas. I never had time for long networking events, so I’d grab coffee with the person I wanted to meet who’d then talk about his or her experience for 30 minutes. Every meeting was valuable and I can name at least one thing I took away from each conversation.

As you begin to build out this network, have at least one financial and legal expert in your corner. Supportive friends and family are important as well, along with other professionals who have already been successful in your industry.

Smart Thing No. 3: I Asked Friends for Help

As a new business owner, I had minimal connections and certainly no clients. Luckily, I quickly found that friends are always willing to help.

A good friend of mine, who’s also a lawyer, was happy to look over and make edits to the online contract templates I found — this easily saved me $500 to $1,000 on lawyers’ fees.


A number of friends came to weekly group workouts for free, so I could get more experience as a trainer. Because of this, I was able to start working with a local gym as a group instructor, which has been important for my success.
The key: You have to ask, which can be hard to do, especially when it feels like you’re putting someone out. But know that, more often than not, friends want to help and be part of your success.

They’re also a great source of positive energy as you trudge through the newness of being a business owner, not knowing what you’re doing from one day to the next.

Smart Thing No. 4: I Worked With the Right Professionals

You may feel like you have to do everything yourself, especially if you’re not yet making money from the business. However, in some cases, it’s smart to hire a professional or pay a friend to do some of the work for you.

I found this to be most helpful with web design and financial management. Both are critical for every new business and I had little to no experience with them.

For example, your business is on a different tax schedule than you as a person. I would have missed the cutoff for a quarterly tax payment — which results in a heavy penalty fine — if my accountant hadn’t reminded me and helped me get it in on time.

Smart Thing No. 5: I Learned From What Didn’t Go As Planned

You’re overflowing with ideas as you watch your passion turn into a business. That’s great; in the spirit of “Just do it,” you should be testing and playing with ideas every day. However, not every idea is going to work out. That doesn’t mean they weren’t worth trying.

“Over the past year, I've failed hundreds of times. I've dealt with it by learning to embrace the failure and the questions that follow. What went wrong? How did this happen? What could I have done differently? What did I learn? And that last bit —learning — is the key. Without learning, it's failure. With learning, it's a step toward success,” explains Tyler Hakes, for

I’ve had many of these moments as well. For example, I was excited to partner with a local juice company four months after starting my business; for $15, people could come to the juice shop, get a full workout and free juice. After just a few sessions, however, I found that people’s schedules were too busy. So it became a challenge to find enough people to make this idea worth continuing.

As fun as it was to collaborate with a local company, this particular avenue didn’t work out, and that’s okay. I can take the knowledge from the experience with me for another partnership opportunity.

Jessica Thiefels is founder and CEO of Jessica Thiefels Consulting. She's been writing for more than 10 years and has been featured in top publications like Forbes and Fast Company.  She also regularly contributes to Virgin, Business Insider, Glassdoor, and more. Follow her on Twitter @JThiefels and connect on LinkedIn. Read More
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