10 Surprising Things I’ve Learned As A New Entrepreneur

Know what you’re getting into so that you’re ready for business ownership.

Shannon Hennig
5 min readJul 15, 2019

You might be thinking of starting your own business and can’t wait to get out there and chase your dream. Everywhere you look there’s advice and stories from those who have had amazing success and you want to join their ranks.

While I’ve had a successful side hustle as a freelance writer and consultant for over three years, my move to full time entrepreneurship is only a few months old. It’s been an exciting journey and there have been a lot of great lessons learned.

Reflecting on my experience so far there are ten things that have surprised me about the reality of running a business that I want to share.

The highs are very high and the lows can leave you wondering what you’re doing, but the advantages of working for yourself are priceless.

  1. Business development never stops.

Once you land a client or two and get head down in paid work, you might think that you’re set. For the short term you’ve got a source of revenue, but a month or two down the road you’re going to need more projects.

Networking, sourcing potential leads, drafting proposals, and regularly promoting yourself are all part of the game. Building your client base is an ongoing activity if you want to be sustainable and not find yourself without paid work for long stretches of time.

2. Everything takes longer than you think.

When you work for yourself, your attention is pulled in what feels like 100 different directions all the time. While you might think that a task like updating your expenses will only take a few hours, it can quickly turn into an all day affair.

The same rule applies for paid work. Estimate the amount of time you think a project or task will take and then double it. This approach will allow you to plan your time more effectively.

3. Half your time is spent on non-billable work.

At least half of your time will be spent doing things that aren’t billable. This can include things like invoicing, writing proposals, following up on email, and marketing.

If you want to grow your business and bring in more paid work, expect to be doing one or both after regular business hours. The good news is that if you’re really passionate about what you’re doing, a lot of it can feel like fun!

4. Work/life boundaries can be obliterated.

Your passion and drive to succeed might see you crossing the lines of your work/life boundaries on a regular basis. This is especially true if you’re working from home and there’s no physical divide between your “office” and the kitchen table.

The temptation to do more work when you have some down time can be really strong, so it’s important to decide early on what your boundaries are and then stick to them.

5. There’s always just one more to-do.

The list of to-dos for your business will never end. There is always something that will require your attention. As soon as you take care of a few items on your list, you’ll quickly find yourself adding more.

The best way to handle this is to find a prioritization system that works for you. Without consistently managing your to-do list in a predictable way, it will get out of control very quickly!

6. Great client leads can come from the most unlikely places.

Always keep in mind that potential clients could be anywhere and great leads can come from unexpected sources.

Using online platforms like Upwork, Freelancer and FlexJobs are good places to start, but word of mouth and your social network can often bring the best results.

It could be that someone you worked with over a decade ago knows you’re building a business and sends a client your way. Maybe you bump into someone in a coffee shop, casually mention what you do, and suddenly you have a new client.

Always be prepared for the unexpected!

7. Your friends and family might not take you seriously.

Starting your own business comes with risk. There is the risk that it won’t work out or that you lose money. You give up the security of a “job” and exchange it for freedom — which is something a lot of your friends and family might not understand.

If you come from a place where entrepreneurship or business ownership aren’t part of the game this can be especially true. In many ways, you’re breaking the mold when it comes to building the life that you want by not sticking with the usual path to career success.

People will be challenged by this and might think you’re just trying it out for fun. Don’t let their doubt shake your confidence.

8. You MUST plan your day, everyday, or you won’t accomplish much.

Planning how and when you’ll do your work and grow your business is absolutely essential. Prior to starting on my own I could get away with having a rough idea of what I wanted to accomplish in a day. Business ownership has completely changed that.

Without a solid plan each and everyday you’ll quickly get distracted. Your attention will get pulled away by other tasks that are just as important as the one you’re currently working on.

Use a time management system that works for you, but just make sure you’re creating a plan that you can follow through on. Don’t over commit to the number of things you want to accomplish and remember to schedule time to take breaks.

9. Setting goals and targets is invaluable.

Whether it’s revenue targets, business development goals or ROI on your marketing efforts, having a clear set of goals and targets you want to achieve will help keep you focused.

When setting your targets, remember to build in a system to track your progress and assign milestones to each. The more detail you can work into these plans, the more information you’ll have to analyze and identify areas where you can improve.

10. Tracking your time will make you more productive.

When you pay attention to where your time and energy flow, you’ll get a better idea of how to plan and schedule your day to day operations.

Tracking your time can show you areas where you’re dedicating the most of your resources and can help improve your productivity. For example, if you find that writing proposals is taking you an incredibly long time, you might start to consider the time of the day you’re sitting down to work on them.

Your energy and focus are at their peak in the morning, and then naturally ebb and flow throughout the day. If you’re consistently trying to write your proposals after lunch, you’re going to be fighting fatigue. Or it could be that you need to carve out a dedicated two hour chunk of time to focus instead of trying to do the work in small bursts.

Entrepreneurship is an exciting journey — one that can bring you incredible rewards. Go in with your eyes open, be ready to work hard, and remember that you’re in it for the long game. You’ve got this.

Join my community of entrepreneurs and creatives by clicking here. Boost your productivity, balance work and life, and move closer to self employment.

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Shannon Hennig

Communication strategist and writer. Mindfulness, health, wellness and being a busy working mom.