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8 Hard Lessons Learned in the First Year of a Startup

5 Mins read

What is the hardest lesson you learned during the first year of your startup business?

Starting your own business is a massive undertaking, with a lot of trials and tribulations along the way. The good news is, you can avoid some hard-hitting mistakes by taking to heart the lessons these eight entrepreneurs learned during the first year of establishing their startups.

  • Established Startups Aren’t Immune to Relaunch/Rebuild
  • Have at Least Two Years’ Worth of Reporting Before Going All-In
  • Plan for the Unexpected
  • Adapt Accordingly to Inevitable Change
  • Set and Maintain Clear Boundaries
  • Learn to Delegate
  • Be a Leader, Not an Order Taker
  • Keep Focused on One Exceptionally Executed Goal

Established Startups Aren’t Immune to Relaunch/Rebuild

I became the owner of a startup in 2020, right before the pandemic hit. I had spent the previous half-decade helping to build that business as an operations manager before taking over the helm. Then, museums shut down, businesses went remote, and our main revenue stream disappeared, quite literally, overnight. I spent the next month and the following two years building a new brand from next-to-scratch.

One of my most surprising lessons as a first-year business owner was that taking the reins of an established start-up is not a guarantee for avoiding having to build a company from the ground up. While the pandemic itself was no blessing, in a way this massive overnight shift was slightly fortuitous because it allowed me to rapidly implement a new vision for the company and make it my own much more quickly than if I had enacted change gradually.

Tasia Duske, Museum Hack

Have at Least Two Years’ Worth of Reporting Before Going All-In

I was so excited to run my own business and not have to report to clients that, when I showed the first hints of financial success within just the first several months of my startup, I wrapped up the stable work I had with clients and invested 100% into my business. Well, for me, it turns out that a lot of the income from my business is seasonal. I had let go of my clients when my business was at its peak for the year, and I had made the assumption that those good months were going to continue to last.

I ended up eating into more savings than I had hoped, and I had to live an extremely frugal year in order to spend less than I was earning. The lesson I took away from this, and have applied to future businesses, is to have at least two years of reporting to determine any seasonal fluctuations and to be ready to take into account those fluctuations when it comes to expenses.

Kristine Thorndyke, Test Prep Nerds

Plan for the Unexpected

You should have a back up plan for as many potential issues as you can fathom. The first year of a new business venture can be incredibly delicate. Sometimes it only takes a bit of bad luck to put your goals on the back burner and shift you into recovery mode. One thing I learned was that you should always plan for unexpected circumstances.

Even when everything is going right, it’s a good practice to consider what you’d do if things went wrong. Have alternate options set up and ready to go, or in the very least research all options pertaining to your business’ needs so that you’re ready to react if crucial plans fall through at the last moment. You can’t prepare for everything, but every precaution you take is one more potential disaster you’ll be able to survive.

Boye Fajinmi, TheFutureParty

Adapt Accordingly to Inevitable Change

The most difficult lesson I learned during my first year as an entrepreneur is that change is inevitable, and every business needs to be able to adjust seamlessly. It can be easy to overlook the fact that once you become comfortable with your business plan, it may change suddenly depending on factors beyond your control. By being able to face this challenge calmly, the better you’re able to bounce back from any difficulties that may arise.

Jonathan Zacharias, GR0

Set and Maintain Clear Boundaries

One of the most essential lessons I learned during my first year as an entrepreneur was to learn how to set boundaries. Boundaries are essential in every aspect of life, but if you really want to succeed (and save yourself from future headaches) don’t be afraid to set boundaries! Boundaries can be set with clients regarding their expectations, your working hours, your working style, etc. While it might be awkward at first for some, setting boundaries in every aspect of your work life will allow you to maintain a balanced life as an entrepreneur.

Rich Rudzinski, Tragic Media

Learn to Delegate

The hardest lesson I learned in my first year of business was the importance of delegation. When you’re first starting out, it’s easy to try to do everything yourself. You want to be in control of every aspect of your business, and you don’t want to have to rely on anyone else. However, as my business started to grow, I quickly realized that I couldn’t do everything myself. I needed to start delegating tasks to other people if I wanted my business to continue to grow. It wasn’t easy letting go of control, but it was essential for the long-term success of my business.

Lorien Strydom,

Be a Leader, Not an Order Taker

My first content writing client had very specific requests for their content. It was almost like having a checklist of things to write or include. That made it easy for me to make them happy. I made the mistake of using that experience as a benchmark, when in reality it was an anomaly. It wasn’t until months later that I learned the difference between being a valuable partner to a client vs. being an order taker. I realized I could make a greater difference (and more money) when I led conversations with prospective clients and enriched their ideas.

I’ve learned that even clients who say they know what they want might not know what’s best for them. That’s one reason why many of the clients I have now want to work with me. They know I’ll look out for their best interests, make recommendations, and bring new perspectives to their ideas. Anyone can be an order taker, but being the leader is what sets the real experts apart.

Alli Hill, Fleurish Freelance

Keep Focused on One Exceptionally Executed Goal

You need to keep focused. I learned the hard way that the key to success in the first year of your startup business is staying focused on the one thing your business does and not trying to scale prematurely. For example, if you’re building an energy drink business, spend that first year focusing on one energy drink and make it the best out there.

Be the new kid on the block with the best energy drink ever. Tell your customers who you are, why your drink is the best, and then deliver on a great product. If you’re too eager and try to scale to energy bars or supplements, your quality, customer service, and your business will all suffer. It takes a lot of patience and willpower to commit to doing just one thing during your first year—but when you do, you’re going to create a highly successful and well-reputed business… and then you can scale from there.

Jimmy Minhas, GerdLi

Brett Farmiloe is the founder of Terkel, a Q&A platform that connects brands with expert insights. Terkel creates community-driven content featuring expert insights. Sign up at to answer questions and get published. 

Startup lessons stock image by GaudiLab/Shutterstock

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