5 Hard Lessons I’ve Learned from 30+ Years as an Entrepreneur

In my journey spanning over 30 years as a business owner, I’ve encountered my fair share of challenges and triumphs. Through the highs and lows, I’ve learned valuable lessons that have shaped my entrepreneurial path.

In this blog post, I’ll be sharing the top five lessons I’ve learned along the way. These lessons may not be easy, but they are essential for anyone striving to succeed in business.

I’ve been an entrepreneur since the age of 15, and now, at 50, I bring decades of experience to the table.

From launching my own clothing line and dance studio before I was 20, to exploring interior design, art and personal training my entrepreneurial journey has been diverse and dynamic.

Finally, I became a therapist and a coach. While I initially envisioned a lifelong career in therapy and coaching, life had other plans. Amidst a period of grieving the loss of a loved one, I discovered photography, which made me change my career path once again, and has now defined my work for the past 15 years.

Did I achieve success with every business I started? Certainly not. Like most entrepreneurs, I experienced my fair share of trial and error. I learned by doing, embracing each challenge the best I could.

Looking back, I have no regrets. I’m thankful for every failure, and setback I had along the way because those were the moments I truly learned some valuable lessons.

You seldom learn from your successes, right. It’s through falling, pushing, breaking, and trying that we acquire the most profound insights and forge our path to success.

Will I ever consider changing career path again? Absolutely!

I’m a strong believer in following your heart – no matter your age. So if my heart tells me to go for something new, I will definitely consider it.

For the past 15 years I’ve worked as a photographer and I’m super committed to my craft. Photography still make my heart sing, so I have no desire to change career.

But maybe when I’m in my 70’s I’ll start teaching yoga instead of photography. As long as I fill my days with something that brings me joy and fulfilment, it’s all that matters. I want to be open to changing and walking new paths even though I’m getting older.

5 Hard Lessons I’ve Learned from 30+ Years as an Entrepreneur

Are you ready? Here we go!

#1. It’s From Our Struggles That We Grow The Most

One thing I’ve learned is that there’s no single “right” way to start a successful business; it’s all about trial and error.

The truth is, that there’s nothing to be afraid of. Whatever happens, you will handle it as you walk through it.

When you face new challenges in life, you will discover new resource within you that you never knew you had. And that is a beautiful thing. You GROW from it. You become stronger from it.

From a young age, I’ve heard my mom dream about opening her own yarn shop. She’s always been an incredible knitter, crafting unique patterns and styles. Whenever she spoke of her dream, her eyes sparkled and her voice softened. My sister and I have always encouraged her to follow her dream, but sadly, she never summoned the courage to pursue it. Now, at 75, she has regrets.

When I recently asked her why she never chased her dream, she confessed, “I wasn’t brave enough. I was afraid it wouldn’t work out.”

But here’s the truth: Failure is a gift. It may come wrapped in ugly packaging, but it’s still a gift. It’s from our struggles that we experience the most growth, so we shouldn’t be afraid to take chances. It’s better to take risks than to regret missed opportunities.

When it comes to startup entrepreneurs, I believe they fall into two categories: those who overthink and struggle to take action, and those who dive in without fully strategizing.

I’d definitely consider myself in the latter category. In my younger days, I was like a bull running towards my goal without fear and without thinking too much if it was a good idea.

I was excited and inexperienced in business. Consequently, I encountered my fair share of obstacles, but each one made me better for my next business move.

As I’ve matured, I’ve become more reflective and less impulsive. I no longer rush into action because, I value my TIME more today, than when I was younger. I want to ensure that any new goal/idea aligns with my values and life purpose before committing.

I’m still jumping into unknown territory even when I’m afraid, if it aligns with how I want to live my life in the future. I embrace any challenges that might come.

I know setbacks and struggles are inevitable on the path to thriving. And I love the idea that I will come out on the other side; even wiser and more resilient.

So don’t let fear hold you back from starting something new, even if you don’t have everything figured out. You’ll learn as you go. It’s all part of the journey toward excellence.

#2. Self-Discipline Is How You Get Things Done

Business success doesn’t happen without effort and pushing through. That’s why we need to train our self-discipline. Without self-discipline, we won’t be able to create the changes we desire in our lives.

Unfortunately, self-discipline is not something that we’re born with, but rather a skill that we can develop and strengthen over time.

Self-discipline allows us to align our actions with our goals and push through the challenges and distractions that inevitably arise on the path to achieving them.

People who struggle with self-discipline often blame themselves for being weak or lazy, but the truth is that we all face moments of temptation and doubt. It’s how we respond to these challenges that determines our success.

When we give in to excuses and laziness, we allow our excuses to dominate and shape our lives. On the other hand, when we push through even when we don’t feel like it, our bodies and minds start to cooperate and adapt.

In other words; our self-discipline is the key ingredient in crafting our business prosperity.

I clearly remember a period of my life I’d like to call; the “lazy days of my entrepreneurial life”. I was in my late twenties, and I felt I had all the time in the world.

I would get up late, meet for coffee with other self-employed friends, I would do some research online to get new inspiration, watch some TV, look through social media, and think of new ideas.

I wasted so MUCH time not having a clear strategy and plan with my business. But that all changed in 2010 when I enrolled in B-School with Marie Forleo. Never before in my life had I met a person as goal dedicated and disciplined as her.

I started planning my workday, the night before. Making sure I had a clear to-do list when I woke up. I made half-year plans, business plans and content creation calendars. And I started systemising my work routines, so I could produce more effectively. And to my surprise I discovered that I liked being this structured.

Self-discipline isn’t easy, and it requires effort and determination. It’s about doing the hard things that we know are good for us, even when they’re outside of our comfort zone. It’s about taking action and being willing to learn and possibly even fail along the way.

Self-discipline helps us stay on track despite temptations, push through obstacles and self-doubt, and overcome challenges such as pain, boredom, distraction, fear, insecurity, and doubt.

It allows us to feel strong, brave, capable, and in control. In a world full of distractions, self-discipline is what keeps us focused on our goals and helps us push through moments of boredom that can kill our dreams.

When I decided to make my first online course, I my three kids were 5, 6 and 10. I quickly discovered how time demanding it was to create a course and I struggled to find the time between my photography job, house chores, cooking and motherhood.

I realized I had to change behaviour to reach my goal. I had to be very disciplined about HOW I spend my time.

I started getting up at 5 in the morning to get work done before the kids got up. I skipped watching TV and meeting friends for a few months. I also arranged for a baby sitter to take my kids every Friday after school, so I would have a full day to focus on work.

Changing my work habits was a game-changer for me personally, as well as for my business. I got so much done, and my business really started to grow!

I learned that the key to achieving your goals is to take action – even when you don’t feel like it. And then when you get momentum, motivation starts to appear naturally and you no longer have to rely so heavily on self-discipline.

Self-discipline is the one tool that will always help you propel towards success.

#3. Don’t Give Up Because You Meet Rejections

Every successful business owner have a lot of no’s, failures and rejections behind them. Now I’m not saying this to take your courage away; I’m saying it to remind you that rejection is normal and you can’t take it personally.

When you get a no, it doesn’t mean there’s something wrong with you or your offerings. A rejection is valuable feedback, telling you that you either tried to work with the wrong person or need to change your strategy. It doesn’t mean that you are incompetent, stupid, or a failure.

Every no is feedback. Every rejection is feedback. And every failure is feedback teaching you to look at new ways to do things. Your job as a business owner is to find the strategies that work for your business.

Don’t give up because a few people don’t like what you offer. Don’t give up because you meet rejections. It’s all part of the road to success.

For every no, you are one step closer to getting a yes. And when you get your first yes, you gain momentum.

#4. Invest In Your GROWTH and Your SKILLS

My next tip is to invest in yourself – not your business. This takes a bit of explanation. One of the biggest mistakes I see creatives make is that they invest all their time and money into their business right from the start but not always in the right way.

They want the perfect website, logo, workspace, and more tools and equipment than they actually need. The truth is that this rarely brings in customers. So when you finally have the perfect setup, the customers and clients are a no-show.

I’ve been there too. This is a normal first-move strategy when you are new to business. But often, all these investments are covering up for the business owners’ insecurities.

I cannot tell you how much money I have wasted in my time as an entrepreneur on expensive web design, business cards, flyers, logos, workspaces and strange gadgets to impress my clients, like pens and coffee cups with my logo on.

Not to mention all the camera equipment I bought that I never use, but I bought it because I thought it would help me look more professional.

I’m not saying that all those things are not important. But it’s not the best place to put your savings in the first few months of your business.

The truth is that your customers and clients don’t care about those things. They only care about how you can help them.

They care about how you serve them and how you make them feel. They want to know if you can make a difference in their lives with your service and products.

So the best place to invest your money and valuable time are to invest in YOU and your skills. Invest in learning the right skills.

Learn HOW to communicate what your offer in the most attractive way possible. Learn how to ask your customers questions that open up conversations that lead to a sale. Learn how to connect with people and inspire them with what you offer.

Invest in courses that help you become so good at your craft that you can’t be ignored. Invest in coaching so you can get support and overcome your struggles faster than your competition.

Invest your time in networking online and offline. Talk about what you do with passion to everyone you meet. That’s one of the best ways to get real customers.

Yes, the website matters and you should have a good profile photo of yourself too – but you can start with a single page website that you build yourself.

Even a Facebook page or an Instagram page will do the job. And then when you have the ball rolling and money is coming in, you can begin to invest more into your business.

#5. Learn To LOVE Selling

How do you feel about selling your products or offerings?

Perhaps you know that nagging fear of putting yourself out there, the fear of becoming a sleazy salesperson, the fear of stepping outside of your comfort zone and ask for the sale. The fear of no one wants to buy your products.

It saddens me to see how many creatives give up on their dream because they struggle to sell.

They blame themselves, lose confidence and doubt if they are good enough – when really, what they lack is effective key strategies for selling their products and services.

So if you recognize yourself in the above – do NOT feel like a failure! I bet about 95% of all creative business owners deal with the fear of selling and putting their offerings out there.

As I said earlier, no one starting ballet today will dance professionally on stage tomorrow. How can you be a world-class sales queen when no one never taught you how?

If this is your first time running a business in your life how on earth should you know how to sell and make profit successfully?

I know the feeling. I ́ve been there. It took a huge shift in my focus and a major shift in my thinking to understand that selling was the key to not only business survival but to business thriving.

Selling is, without a doubt, the most challenging part of running a business. After all, we got into this business for the love of our craft, not because we love selling.

But then we realize that in order to survive, we need to make offers to people. We need to sell to make money otherwise, we just have a really expensive hobby, right?

And when we start out as newbies, we are so happy just to make a little money and we tend to charge small fees – only to find out that small fees hardly cover our expenses.

We realize that we need to opt our game, raise our prices and start selling more professionally to hit the big income goals.

Selling is much more about relationships, compassion and inspiration than it’s about hard-core sales strategies because selling is all about connecting with your perfect audience and showing them that you are the best fit to serve them.

And let me just remove one of the biggest misconceptions many creatives have about selling; that it takes confidence to sell.

I often hear this “I don’t have the confidence to sell my products” or “if only I had more confidence, I would promote my offerings.” The good news is that you don’t need confidence to sell.

The number one reason why so many struggle to make money in their business is that they don’t show up. They hide, thinking it’s so much easier to play safe and color so far inside the lines that they don’t stand out as being too much.

As humans… we crave safety. It’s one of the top human needs. We need to feel safe. So when presented with the idea of getting out from our hiding place to sell… it can feel terrifying!!!!!

Perhaps you know the feeling. You want success with your creative passion, but you avoid showing yourself to the world – hoping that one day will be your lucky day and someone will discover you.

And you wait around, hiding in the shadows, hoping your confidence will magically appear someday…

Someday, I will put myself out there…
Someday, I will promote my products…
Someday, I will ask for the sale…
Someday, I will show the world how great I am…

But here’s the truth; visibility is critical to the success of your business: people can’t pay you if they can’t find you.

“Someday”, will not make you a profitable + successful business.
“Someday”, is an excuse to hide and play small. YOU are better than that! YOU deserve more!

You have SO MUCH to offer. And it doesn’t do anybody any good if you keep it to yourself. You got to decide that you’re done with disappearing into the background. You got to step out into the light.

But don’t worry; you don’t have to be a sleazy salesperson! There’s no need for icky sales pitches! Instead, talk about the experience customers will get from working with you.

Tell them how it will make them FEEL. Explain ALL the benefits of your service or product. Explain the process of working with you and show your passion for what you do.

Nothing sells better than passion and excitement! Customers will be drawn to you like a magnet when you show up to inspire, serve and spark meaningful conversations.

Shift your thinking from believing you are an annoying salesperson to thinking you are a helper. Believe that you can make a difference with your products or offerings.

Think of ways you can HELP and serve your clients and make their life better. From that state of mind, it is easier to sell from the heart.

Selling is not about being annoying or forcing your products on someone. Selling is LOVE. If you love what you do, all you sell is LOVE.

Selling is sharing inspiration. If you feel inspired to inspire others, all you sell is an inspiration.

Selling is storytelling. Forget icky sales emails. Talk about your journey. Share how you got from where you were to where you are today.

Share how you overcame your struggles and how you are now ready to help people in a similar situation as you once were.

Be passionate about what you do and what you offer and share your excitement.

That’s it. This blog post got a bit long, but I hope it was helpful and inspiring to you.

With love, Christina

About Christina Greve

Christina Greve is an experienced Photographer, Educator & Mindset Coach with a passion for flowers, decorating & country living. She's the founder of The Lifestyle Photography Academy + The Empowered Creative Show. She provides tools, education and inspiration designed to help multi-passionate women, artists and creative souls find direction, push through self-doubt + make a living doing what they LOVE.She is known for her elegant storytelling photography and draws much of her inspiration from the Nordic countryside, travels, food and still life.Her work has been featured in numerous magazines, blogs and books worldwide. After a decade of working with psychology, Christina's passion for photography evolved into a full-time photography and coaching business.Today she runs a thriving + fast-growing international empire specializing in professional online training, motivating and engaging female photographers, designers, bloggers, makers and creatives. She has coached thousands of fabulous women from more than 40+ countries.With her Podcast "The Empowered Creative," her popular Instagram posts, and quickly sold-out workshops, Christina has become the go-to person for many creatives seeking like-minded sisterhood, real support and heartfelt encouragement.