10 Life Changing Lessons I’ve Learned as an Entrepreneur

Lindsay Carter |

10 Life Changing Lessons I’ve Learned as an Entrepreneur

By Jason Silverberg, CFP®, CLU®, ChFC®


Are you considering quitting your job and becoming an Entrepreneur? Maybe you’d like to become a real estate agent, start your own consulting business, or even own a restaurant. Whatever your passion, the allure of being your own boss and setting your own schedule can be quite enticing. At the same time, starting out can be hard and going at it alone can get quite lonely.

I started my practice in 2005, helping my clients achieve their financial dreams and goals. I’ve experienced some big challenges and had a lot of successes. I’ve met many different types of people and learned many life lessons throughout my journey.

If you’re considering becoming an entrepreneur, pay attention! Here are 10 life changing lessons that I’ve learned that have helped me grow my business and my skillset.


1. It’s not what you know, but who you know that matters

As you start your new business venture, the most critical piece to your success will be gaining new customers and clients. You can start out by sharing your business idea with your friends and family, but you’ll need to expand beyond this if you’re wanting to grow.

The network of people that you surround yourself with can be instrumental in the success of your business. People buy from people they know, like, and trust. If you can borrow credibility from the people in your network, and have them advocate for you and your business to the people they know, then you might be able to gain some traction.

Word of mouth marketing, or referral marketing, is the number one way businesses grow. As you network with other people, always be giving. People won’t buy from you if it’s always about you. Give away free samples, add-ons, or promotions. Link up with other professionals to provided value added seminars and combo packages. If you expand your network, you’ll expand your business.


2. To speak or not to speak

Public speaking is often rated as a top fear amongst Americans. You might be thinking that since everyone is watching you that if you mess up, they’re all going to laugh at you.

In reality, many of these fears are in your mind. Public speaking is a critical skill that when used appropriately, can broadcast your message to a wide audience. It can be fun and interactive and can also bring in new customers or clients to your business.

Be sure to make your presentations educational and not salesy. At the same time, always offer a call to action, to capture potential clients. Use more pictures and stories to hit your point, rather than reading text off a slide.

To build your skills, join a Toastmasters group. Practice in front of a mirror or with your friends or family. Video tape your presentations and watch the footage back. Just like with anything, practice makes perfect. Honing this skill can prove fruitful as you build your business.


3. Watch your budget

Since you don’t have a steady paycheck of your own, you’ll need to watch your cash flow like a hawk. Some months you might have a huge influx of income and other months might be slow. Be disciplined enough to save the extra money in reserves to be used when times get tough.

Knowing your fixed and variable expenses will help you identify profit or loss. As you spend money on marketing projects and other business ideas, track your numbers. Know when a venture is running in the red and when to cut it lose. Sometimes you might keep the project going as a loss leader, if it brings value to another end of your business.

Don’t forget, you still have to eat. Be sure to review your personal budget too. Having a large emergency fund can help you wade through hard times and keep you out of debt. Knowing these numbers will be help you make smart financial decisions.


4. "Shoot for the moon. Even if you miss, you'll land among stars!” – Les Brown

As you build your business, it’s a good idea to start with the end in mind. Having a big vision for your business can help you focus your efforts in the right direction. A business without clarity of purpose and direction will become distracted and fall apart.

Don’t be afraid to have a big vision. Many first time entrepreneurs are reluctant to set big goals. If you’re one of those people, you’re probably afraid that you’re not going to hit them. Remember this is the ultimate direction of your business. This isn’t something you have to achieve tomorrow. The bigger your thinking, the bigger you can grow.

Sometimes the mere exercise of setting big goals sets off a chain reaction that makes it a self-fulfilling prophecy. If you didn’t set those bigger goals, you probably wouldn’t have created your business plan in the same way. You would have played in the shallow end of the pool and never gone after bigger fish. Bigger thinking can bring bigger results.


5. Working on the business is different than working in the business

As you grow your business, you’ll need to make time for strategic planning. This is the time that you spend working on your business goals and broader marketing plans. You might convince yourself that if you’re not working in your business, then you’re not doing your job. While you should be spending the majority of your time being the technician and getting the job done, it’s critical to carve out time to put on your business owner hat and work on planning objectives.

As you create your strategic plan, connect with your long term vison. Imagine your business 3 years from today and work backwards to figure out where you will need to be 1 year from now to be on pace to hit those goals. Then take it one step further and consider where you’ll need to be 90 days from now. Finally, break your plan into weekly tactical action items. These are morsels of work that, when accomplished, further your long term vision.

You might need to get out of your office or usual workspace to do this type planning. Not only will you eliminate distractions, but your mind will be freed up to tackle these broader challenges. Even though strategic planning takes you away from the day-to-day functions of your business, it’s critical to the growth of your business and long term vision.


6. Be comfortable being uncomfortable

Starting your own business can get quite uncomfortable sometimes. You’re building new skills and putting yourself in situations that you’ve never been in before. Just like with weight lifting, no pain, no gain.

Being uncomfortable means that you’re growing and learning. These are all good things. Embrace this feeling and know that you’ll come out the other end with knowledge and experience that will help you in the future.

Don’t be afraid to make mistakes too. Mistakes hurt your ego, but if you learn from them, they can be vital to your success. Making mistakes is also a sign that you’re challenging yourself and moving out of your comfort zone. Certainly address the mistake, so it doesn’t happen again, but know that in the end, it’s going to be okay.


7. Have a Positive Mindset

Much of your success will be attributable to your mindset. With a dire outlook to the future, there’s no way you will be able to withstand tough times. Staying positive and optimistic will not only make you more attractive to your clientele, but also motivate you to continue the uphill battle.

Be careful with who you choose to associate with. You might have a business partner or strategic relationship that can influence your mindset. Stay true to yourself and your vision. Spend time feeding your mind positive self-talk and invest in motivational tools. Read books and listen to podcasts.

A healthy body is the key to a healthy mind. Don’t forget to spend time exercising, doing yoga, or even meditating. Eat healthy and wear nice clothes. You’d be surprised how good you’ll feel and how much of impact it has on your business, if you make small steps toward living a healthier lifestyle.


8. Manage your time, or it will manage you

Being your own boss has some major perks. One of the biggest benefits is not being chained to a desk from 9am to 5pm. While this can be quite liberating, it can also be quite overwhelming.

You might be someone who craves structure. Without a set schedule, you could have difficulty managing the calendar. It’s common for someone to get lost in the sea of time and work on unprofitable activities just to stay busy.

Time blocking might be a good strategy to keep your schedule organized and on task. Setup times for specific activities in your calendar, along with revenue generating activities and strategic planning blocks. This way, you will ensure that each of the items will get accomplished.

Be sure to stick to the schedule and don’t let distractions creep in. It’s okay to turn someone away politely and ask that they come back later. Consider blocking out time at the beginning and end of your day to reschedule these interruptions and to process email and other administrative tasks.


9. Haters gonna hate

Now that you’re starting to see the fruits of your labor payoff, you might pick up a hater or two. These bullies are negative people who are jealous of your success and feel better about themselves by putting you down. They can come in the form of an anonymous social media commenter or even a close friend or relative.

You might have also experienced these same nay-sayers when you were starting your business. They told you it was too risky and that you’re wasting your time and money.

Every successful person encounters a hater during their career. The best way to deal with a hater is to ignore them and use their rhetoric as a challenge. Use their hate as motivation and prove them wrong. Never let them drown out your passion and enthusiasm.


10. “Be the Change You Want to see in the world” – Ghandi

Ultimately, the work that you do should serve a higher purpose, both to you and the world. Your business should bring something to your life that nothing else can. It should have you launching out of bed each morning with energy and enthusiasm.

Your business should also serve others in a positive way. If you see an injustice or a problem in the world, find a way to solve it. Helping others is the key to a great business. Your work should connect with your “why,” or your life’s purpose. The passion you have for the work you do is paramount to your success.

You might be helping people become better versions of themselves or just simply finding ways to put a smile on their face. Either way, you never know the ripple effect that you might have on someone’s life and how that can change the world.


In my book, The Financial Planning PuzzleI discuss these lessons and other tips for small business owners. Buy the book now on Amazon.com here.

If you’d like to discuss your own personal finances, you can email me directly at jason@finadvinc.com or call me at 301-610-0071.




Jason Silverberg CFP®, CLU®, ChFC®, specializes in compressive financial planning. His practice aims at helping families and small business owners to fit their financial pieces together to create financial freedom. He uses a values-based process to connect with his clients on a deeper level than some advisors, diving into the “why” behind the numbers. He focuses on helping clients achieve and protect their goals through methodical investment strategies and calculated risk management and insurance solutions. Jason is a registered representative and investment advisor representative of Securian Financial Services, Inc. Member FINRA/SIPC. Financial Advantage Associates is independently owned and operated. Separate from the financial plan and our role as financial planner, we may recommend the purchase of specific investment or insurance products or accounts.  These product recommendations are not part of the financial plan and you are under no obligation to follow them.

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