The 5 things I’ve learned from restarting my business multiple times in 5 years

Jen Lister Strategy - 5 years in business

This is the first business photoshoot I did with my husband back in 2021 - so much has happened since then!

Reaching 5 years in business is a milestone I’m celebrating, but if I’m being honest, it has been a rollercoaster. I want to share the 5 big lessons I’ve learnt in these 5 years.

Ten years ago I stepped away from my ‘successful’ corporate career and became a business owner. It was a scary step, but something that I’d always wanted to do. I had this fire in my belly to run my own business, but I had no idea on the how…

Since then I have built a franchise business, a networking community, a property business, a network marketing business, and of course, my own Strategy business. I have worked in business partnerships and as a solo business owner. I’ve sold, shut down and quit businesses. I’ve experiences so many highs (like winning awards, working with incredible clients and selling out events) and plenty of lows (like having next to nothing in my business bank account, navigating difficult client situations and feeling imposter syndrome).

The last 5 years have been so important though. And that’s because I have grown my Strategy business alongside the backdrop of growing our family. This has involved having 2 children, getting married, building an extension (not with my bare hands!) and navigating the craziness that life throws at you. Oh, and my husband also started his own business as a photographer in that time(!).

The result of the children has meant I have literally restarted my business multiple times, and as a result, there are so many lessons I want to share from my journey. Here they are:-

1. Word of mouth is marketing magic

Word of mouth is the most beautiful way to grow your business. Here’s why: vibes attract vibes. When you deliver an exceptional experience for a client you love, and they recommend you to their network, the people who come through that referral share that same energy, values, and work ethic. You end up filling your business with dream clients without having to slog away on social media 24/7.

However this does take time. From my experience of running multiple businesses over the past decade, and very much building a part time business around my family, it takes around 12-18 months for word of mouth to truly take effect. It takes this time to build up your reputation, credibility, and relationships. And it is absolutely worth putting the time and energy into this.

“Getting those first few clients can feel tough, but if you really nurture them, and deliver an exceptional client service, the knock on effect is a business that feels aligned and brings you that momentum you’ve been dreaming of!”
— Jen Lister

2. Embodying the 3 core characteristrics for success

I get a lot of emails in my inbox, but one email I look forward to reading every single month comes from the brilliant Dr. Hayley Lewis - an organisational psychologist and business friend of mine.

Her evidence-based research into female entrepreneurship highlights key personality factours which were more likely to help female SME owners to succeed in business:

  • Self-Efficacy: In simple terms, this is about backing yourself and actively promoting what you do. It’s the belief in your ability to step up, put yourself out there, and show people how you can help them. Yes, it can feel uncomfortable, but it’s essential and practicing this (e.g. at networking events) definitely helps.

  • Resilience: This is about being able to adapt to changing circumstances, deal with difficult situations and work towards the bigger picture in your business. There are always going to be setbacks, but knowing you can respond and grow from these experiences is key.

  • Creativity: Many people assume that when you run a business, you can’t be creative, but I disagree. Creativity in business is about how you solve problems, innovate your offers, and adapt. Business without creativity would be pretty boring, and I find a great way to foster creativity is to go out on a walk in nature.

Take some time to think about how you can build on these 3 characteristics in your business and use them to your advantage.

3. Give yourself a break when it comes to socials

Guess what? Nobody thinks they’re doing social media ‘well enough’, so stop worrying about it! Showing up on social media is, without a doubt, the number 1 thing I hear my clients struggle with. They feel nervous about speaking to camera, they spend hours recording content that never sees the light of day, and they worry what other people think. I know I have struggled with all of this in the past (and sometimes I still do!), however I have finally decided that I don’t care what anyone thinks anymore. Their opinion doesn’t matter, because they aren’t living my life, paying my mortgage, or taking me on holidays!

After 5 years, I’ve finally reached the point where I just don't care about the judgment! Recently, a client said to me, "I don't know how you show up like that on social media." I took it as a huge compliment - because that level of ease didn't happen overnight. It took 5 years of practice. If I scrolled back to my content from the start I’m sure I’d cringe!

Almost nobody thinks they are doing social media well enough. Out of all the business owners I know, I can count on one hand the ones who feel really confident. Having to market our businesses on public platforms in real-time is completely unprecedented—our brains weren't built for this!

So be kinder to yourself. Have a simple, sustainable strategy in place, but give yourself permission to go with the flow and actually enjoy it.

4. Find your tribe

You cannot build a successful business in isolation. Running a business is brilliant, but there will be days when you feel like quitting. When those messy moments hit, having the right support system around you is the difference between throwing in the towel and pushing through.

When I started my first business back in 2017, I was blessed with wonderful friends and family, but hardly any of them ran their own businesses. As much as they loved me, they couldn't truly understand the specific pressures of entrepreneurship.

When I started this business in 2021, everything was different. I surrounded myself with a community of fellow business owners - women who quickly became real friends. Having that tribe to lean on, celebrate wins with, and text when things got tough completely transformed my self-belief. Find your village. It is non-negotiable for long-term success.

5. Start with a strategy and stay obsessed with the sale

If you want to build a business that lasts 5 years and beyond, you cannot just wing it. You need a plan. 44% of businesses cease trading after 3 years (Source: Office of National Statistics), so pushing through that tricky 3rd year is definitely key to success.

So what is a strategy and why bother? Your strategy doesn’t need to be a 50-page document, but you must know what you stand for, who you serve, and how you deliver value. Having a clear strategy is the secret to showing up consistently, attracting your dream clients, and repelling the wrong ones.

Once your strategy is set, focus on the sales. To sell effectively, you must be crystal clear on your offer, your pricing, and the transformation you deliver. The most precious asset in your business (after a loyal client) is an enquiry - make sure you nurture these with care.

In the beginning, sales will trickle in. But as those initial clients experience your magic, word-of-mouth momentum kicks in. That trickle turns into a steady stream of dream referrals, allowing you to build a sustainable, profitable business that fits around your life.

📩 Ready to Build Your Full-Time Income in Part-Time Hours?

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👉 Click here to book a 1:1 discovery call with me today and let’s map out your roadmap!

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