8 Lessons Learned from Starting My Own Business

Let me open up the curtain of entrepreneurship for you on my own business journey, and share 8 lessons that I’ve learned from starting my own business.  Some of these lessons went down easy, while others were harder to swallow. Hopefully your own journey of entrepreneurship can be just a bit less bumpy with this information.

First things first.

1. Takes longer than you think.

I smile remembering the moment that I gave the web guy the go ahead that the website could be officially published on my site to officially offer coaching services, book a call with me, and start making money on my soon to be new career.  It was New Year’s Eve 2019. We were out to dinner as a family before heading over to a family friendly NYE party complete with fireworks.

The scheduling system was synced to my calendar.  The website buttons to schedule a call were linked, the blog posts were transferred to the new site, and the free lead magnet was ready to roll. The nervous anticipation was palpable.

The website went live, and I made a social post about the new site – and waited for my alerts to blow up with booked calls. That never came. 

My website hasn’t ever been a strong driver of new clients. In fact, it took me six months to book my first paying client. You read that right, SIX months. 

Did I second guess everything I was doing? I sure did. But instead of giving up I remained consistent, I made clear for myself what I was doing, and why. 

LESSON: Plan on your business to take much longer than expected to get off the ground. If it happens earlier, great! 

2. Have a why bigger than yourself.

Listen, it’s not enough to pick a new career for yourself because it sounds nice, it’ll pay the bills, or you’re good at it even. I mean, those are good too – but it has to be bigger.

And I’d say that it should be bigger in more than one way.  Let me explain.

Why do I coach?

First pass answer is it allows me to make a meaningful impact on others, while allowing me the flexibility to have more time with my family.

That’s a fine answer, but truly – it’s not enough.  Why else?

Part one. 

I know from the bottom of my bones that coaching people through the challenges of small business and money management can change their lives not just in the present, but for a lifetime. Like, forever. And that forever will impact the next generation of their family. I absolutely believe in the power of coaching, and the focuses that I hone in are time, talent and money – the most important resources.

Part two. 

Being present, available, and at home when my girls leave for school and get home for the day during this stage of their growing up has been pressed on my heart. I’m not sure that I know exactly what my presence is meant for – but I know that we’ve had more conversations about friendships, boys, and real life between 3-6pm than we ever did before. I’m here for it in this next season of parenthood.

family photo for starting business blog

If you’ve been following this journey from the very beginning it all started with a dream to do life differently and move to an island for a few years, starting with a tiny house in the forest. That all took a pivot when my husband just wasn’t ready to commit to that level of “off the grid”. And what I realized through the unpacking of that dream was that my draw to do life differently didn’t have to end with my toes in the sand – it could still be realized with my toes in the carpet, and a pivot of another kind.

LESSON: Find your deep why, both for your professional and your personal life. The road to fulfilling your why may not look the way you envision it initially, but if your why is big enough – you’ll find the right road to get you there.

3. Be prepared to be new-ish again.

It’s one thing to start a new job, or even a new career – but entrepreneurship is a whole lot of jobs rolled under that umbrella. Like, a lot. 

You are your own accounting, marketing, sales, and delivery team…plus so much more. While you may not be new at the ‘craft’ or service that you deliver the other components are likely to be new for you. Get used to it. Embrace learning and get practiced with failing, and trying again.


Don’t make the mistake of calling yourself a new _______.  It’s quite likely that you have been doing this for years, you just didn’t call it that. So, although new to entrepreneurship don’t send yourself to the starting line of your career field. You have years of experience, use them. 

LESSON: Get your headspace ready to fall down, and pick yourself back up. Be prepared to use Google Search and YouTube for a whole lot of things. Ditch your ego at the door.

4. Set up incremental goals for yourself.

Whether you want to track income, number of items sold, total clients supported, or some other metric – you need to be tracking your stats, and setting up goals for yourself.

How will you know what area that you need to tweak or adjust your pricing, sales process, or client retention if you aren’t tracking it? I want you to track it early and often so that you can catch trends, and make adjustments. I want you to track even when it feels ridiculous to track because you know all of the numbers so intimately. Start the habit early, so that it is a normal practice as your business grows.

Most of us set up income goals for ourselves. How much do you want to make, and by when? Remember what I shared earlier about it taking a hot minute to get things moving. Be gracious in your goal setting, and remember that progress is far greater than perfection. Pay attention to what the data is telling you and take action when things aren’t headed in the direction that you want.

Baby step your way into those goals, and celebrate the heck out of your progress along the way.

LESSON: It’s the habits that move the needle of the bigger goal, set up good habits that support your goals and track them regularly.

5. Pay yourself.

Now, I understand pouring money back into the business initially. I did that for a short time too – but it needs to be short.

Here’s why….we could pour money back into our businesses all.day.long and we can easily talk ourselves into the “takes money, to make money” clique. There are a whole lot of shiny objects out there that would uplevel our brands, teach a new skill, or ease a process – I get it, and I will absolutely recommend that you do this, when the time is right. 

With starting your own business, it needs to support your time. You are not likely prepared to simply volunteer forever doing the work that you do. You have to pay yourself! 

Start by simply giving yourself a percentage based salary. Consider setting aside a small percentage for profit, a bit for taxes, and then wrestle with the remaining percentages between operating expenses and your salary. For every dollar of income that comes in, take it through your already defined percentage based categories. I recommend that you create a budget for your operating expenses too, but that’s not the first time you’ve heard me share the love for the ‘ol spending plan.

Remember that the amount you charge isn’t all “yours” either. 

photographer for starting business blog
Image by diana.grytsku on Freepik

Photographer Example

$1,000 Photoshoot Income

$50 Profit Savings (5%)

$600 Salary (60%)

$150 Tax Savings (15%)

$200 Operating Expenses (20%)

If you start out with a percentage based distribution, it’ll be much easier to have funds available when you need them – and get in the good habits of being profitable, and paying yourself appropriately. Big fan of the ‘Profit First’ money management methodology for businesses.

LESSON: Start as you mean to go. Decide early on that you are going to take a salary, and then stick with it – even if the amount is meager to begin with.

6. Be prepared for added expenses.

Frankly, it’s much easier to work for someone else. They cover the cost of the paper, toner, and office supplies. Most companies will cover your health insurance and dental coverage. All companies will cut a check to the government on your behalf for taxes.

In starting your business, all of these responsibilities fall to you, the entrepreneur. I don’t want you to be surprised by the self employment tax that comes on top of your income tax.

Also, be prepared for insurance coverage – not just the basic business insurance but dental and health insurance premiums for yourself or family. This added expense was a big mental block for us initially, thinking that one of us “had to” keep working traditionally for this coverage. You can certainly purchase on your own, but be aware of the expense.

Matching retirement contributions aren’t as “free” as they used to be on your own, but also possible. Don’t shoot the messenger here, I just want you to be in the know.

I absolutely recommend saving for taxes, annual expenses, and of course your monthly recurring expenses.

LESSON: Starting your business has costs that you may not have anticipated, don’t let them surprise you.

7. Know when to DIY and when to hire.

There is absolute value in knowing the ins and outs of your business, at least initially. I’m a big fan of getting scrappy and learning about how to put together an email campaign, a social media post, and what SEO stands for. Handling your accounting for a period of time is healthy.

There will be a point however, as your business grows that it will make sense to hire out tasks that aren’t in your sweet spot.

Just because you CAN do something, doesn’t mean that you SHOULD.

Sometimes it’ll seem counterintuitive to pay someone for something that you can do, or even that you have time to do – but in order to keep growing your business, you need time and space to work ON the business, not IN the business.

P.S. If you need help in this arena, I’ve created a resource just for you.

I recall hiring my first virtual assistant and passing off scheduling blog posts and creating pins for Pinterest. It was liberating to have those few hours a month back to take on more clients and consider what was next in my business.

LESSON: Don’t be afraid to get scrappy and DIY, but know when to let go of tasks to support the growth of your business.

8. Find your people.

Don’t just find your client/customer people. Those are of course essential to your business; but I want you to prioritize finding community with other business owners. Maybe it’s a networking group, informal group of business owners that swap tips monthly, or formal support by way of coaching, masterminds, or membership.

Find folks that know ‘this side’ of your business and that you can share your ups and downs with for support and strategy. Heck, you can have multiple groups of your people! Entrepreneurship can be lonely, but it doesn’t have to be if you’re intentional about being a support to others, and willing to receive support as well.

LESSON: Get involved with like minded business owners early and often, build relationships! 

Taking it home.

Among those eight lessons that I’ve shared I’ve had my ups and downs with all of them. Being an entrepreneur is hella hard work, but it’s also one of the most rewarding things I’ve ever done.

If you have a burning desire to start your own business, learn the lessons and double down on the work to make it happen. #noregretsonlylessonslearned

Sarah is a Ramsey Preferred Coach
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P.S. I’m now helping entrepreneurs up level their businesses. Start with a low cost $99 assessment and coaching call, no obligation.


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