Starting a Business Again: What I’d Do Differently

This question – it hard, honestly.

Table of Contents

• Lesson One: Build the Business You Want to Run, Not the One You Think You Should Run
• Lesson Two: Sort the Boring Stuff First (It’s Not Actually Boring)
• Lesson Three: Niche Down, Then Niche Down Again
• Lesson Four: Hire Slow, Onboard Fast, and Document Everything
• Lesson Five: Embrace the Slow, Steady Grind (and Protect Your Head)
• Lesson Six: Get Your Digital Presence Right from Day One
• The One Thing I’d Tell My Younger Self
• Conclusion

That hit hard, honestly.

Because I knew exactly what that silence felt like. And I knew that when I was in it, a LinkedIn like or comment wouldn’t have saved me, but a phone call from someone who’d already been through the fire might have.

So when I sat down to write this, I asked myself a question I’ve been circling for years: if I was starting a business again, what would I do differently? Not the polished, conference-friendly answer. The real one. The one that stings a bit to admit.

This isn’t a list of generic startup tips. It’s a candid, sometimes uncomfortable look at the mistakes, missteps, and missed opportunities that shaped my journey. Whether you’re a first-time founder or a seasoned owner planning a reboot, I hope there’s something here you can use.

Lesson One: Build the Business You Want to Run, Not the One You Think You Should Run

For years I chased a version of success that wasn’t mine. Bigger team, bigger office, bigger turnover. I assumed that was the scoreboard. It wasn’t. It was just someone else’s scoreboard, and I’d borrowed it without asking.

If I was starting again, I’d start with the end in mind. Not the exit strategy, but the life I actually wanted. Did I want a sellable asset, a lifestyle business, or a legacy? I never answered that question properly. I just kept running faster.

Values were an afterthought in the early days. The things that matter to me now- balance, charity work with SANDS, travel, time to be a proper dad- were squeezed into the margins. Now they’d be the starting point. There’s a useful mental model in the idea of building to sell, even if you never plan to. But I’d adapt it: build to your definition of success, not anyone else’s.

Every business decision will have detractors. Just like every Star Trek series has its critics, yep, even Discovery, someone will tell you you’re doing it wrong. The key is knowing your own captain’s log, your mission statement, and sticking to it. I once took on a partnership because it looked good on paper. It contradicted everything I believed about what work should feel like. The long-term cost of that choice far outweighed the short-term gain.

Lesson Two: Sort the Boring Stuff First (It’s Not Actually Boring)

Legal, HR, and Contracts: The Unsexy Foundation

I did handshake deals in the early days. I thought it made me a good bloke. It made me a stressed bloke with a solicitor on speed dial. Shareholders’ agreements, client contracts, supplier terms – these aren’t bureaucracy. They’re the walls that keep the weather out.

I’d create a document vault from day one. Insurance, contracts, IP assignments, all in one accessible place. It’s not glamorous, but it saves sleepless nights. And I’d get a good solicitor and accountant before I needed them, not after. In the UK, that means understanding your obligations to Companies House and HMRC from the start, not treating them as an afterthought when the first VAT return lands.

Systems and Processes: Your Business as a Machine

Here’s the meta-lesson: have a process for creating processes. Don’t just document what you do. Create a repeatable framework so that documentation becomes routine, not a heroic effort you do once and never update.

Integration matters too. Disconnected tools create chaos. I’d invest time upfront in choosing a tech stack that talks to itself, avoiding the tech debt that accumulates when you bolt things on later. And systems don’t have to be cold. A welcome video for new clients, a birthday card, a thoughtful onboarding sequence, these are systems that humanise your business.

Budgeting Like a Grown-Up

Cash flow is king. I’d create a realistic budget from day one, not a hopeful spreadsheet with numbers I’d invented to make myself feel better. Chasing debts is uncomfortable, but essential. I’d adopt a bounty hunter mindset: scripts, escalation procedures, and no emotional attachment to the awkwardness.

Personal spending discipline matters too. There’s a memorable analogy about eating canned beans in the early days. I’d reframe that frugality as a strategic choice, not survival mode. It’s easier to make brave business decisions when your personal overheads are low.

Lesson Three: Niche Down, Then Niche Down Again

I said yes to every client in the early days. Every single one. The result was diluted quality, inconsistent messaging, and a team that didn’t know what we stood for. We were a generalist agency in a world that rewards specialists.

Narrowing your target market actually increases revenue potential. A specialist can charge more and deliver better results than a generalist. I’ve seen this work at Delivered Social, where focus on digital marketing for small and medium businesses has built a reputation that a scattergun approach never could.

Saying no is a strategy. I’d have fired bad-fit clients sooner and set boundaries around working hours and pricing from the start. I once kept a client who made every project feel like a root canal. The financial contribution was decent, but the toll on the team was enormous. We lost good people because I was too scared to lose a bad client.

Lesson Four: Hire Slow, Onboard Fast, and Document Everything

I made a hiring mistake that cost me more than money. The financial hit was significant, but the cultural damage was worse. I ignored my gut because I needed someone quickly. I’d have taken more time.

Onboarding is an investment, not an admin task. A structured process with welcome videos, clear role definitions, and a 30/60/90-day plan sets new team members up for success. It also signals that you’re a serious operation, not a chaotic one.

Documentation should be a team sport. Everyone documents their processes, not just the founder. That creates resilience and makes the business less dependent on any single person, including me. HR policies from day one, even with a small team, prevent awkward conversations later. Leave, flexible working, performance reviews – these are easier to establish before you need them.

And invest in professional branding early. A good brand designer is an investment, not an expense. It signals credibility and attracts better clients and employees.

Lesson Five: Embrace the Slow, Steady Grind (and Protect Your Head)

Growth for growth’s sake is a trap. I’d focus on sustainable, profitable growth rather than vanity metrics that look good in a pitch deck but mean nothing on a Tuesday morning.

Mental health and burnout are rarely discussed in these retrospective articles, which is exactly why I’m mentioning them. I’ve been burned out. I’ve sat at my desk at 7 pm unable to remember what I’d actually achieved that day. The strategies I use now – travel, time with family, a proper lunch break, saying no to things that don’t align – aren’t nice-to-haves. They’re the business strategy.

Not every opportunity is a good one. I’d have been more selective about partnerships, speaking engagements, and projects that didn’t align with the core mission. And I’d have built a support network earlier. Mentors, peer groups, even a therapist. Entrepreneurship is lonely, and the DMs I received after my last post reminded me how many of us are quietly struggling.

Lesson Six: Get Your Digital Presence Right from Day One

Your website is your shop window. I’d have invested in professional website development from the start, rather than a DIY template that looked amateurish and cost me credibility. At Delivered Social, we’ve built websites for clients who’d spent years apologising for their old ones. Don’t be that person.

SEO is a long game. It’s not a quick fix, but a compounding asset. I’d have started a blog and built a content strategy from day one, rather than playing catch-up later. The blog network I’m involved with, including Singles Warehouse and Business Pressed, is proof that consistent content builds authority over time.

Social media without a strategy is just noise. I’d have focused on a few platforms where my audience actually spends time, and created content that provides genuine value. The Delivered Social Podcast is a good example of a format that builds community rather than chasing algorithms.

And I’d have started building an email list from day one. Own your audience. Social media platforms can change their rules overnight. Your email list is yours.

The One Thing I’d Tell My Younger Self

It’s not about the tactics, the systems, or the strategy. It’s about confidence and trusting your own judgment. I spent too long looking for permission to do what I already knew was right.

I’d have asked for help sooner. From mentors, peers, professionals. Pride is expensive. It costs you time, money, and peace of mind.

The mistakes are inevitable. They’re part of the process. The goal isn’t to be perfect. It’s to be better. If you’re in the middle of it right now, wondering if you’ve got it wrong, you probably haven’t. You’re just learning.

I’d love to hear your own lessons. Share them in the comments or reach out directly. And if you’re wrestling with your digital presence, whether it’s your website, SEO, or social media, the team at Delivered Social is genuinely good at this stuff. No hard sell, just help.

If I Was Starting a Business Again, What Would I Do Differently – RoundUp

Values, systems, focus, team, wellbeing, and digital presence. These are the pillars of a business built to last. If I were starting a business again, what would I do differently? Almost everything. But also, nothing at all. The mistakes made me who I am today, and they gave me something worth sharing.

It’s never too late to apply these lessons, whether you’re starting fresh or pivoting an existing business. The point isn’t to get it right the first time. The point is to keep going, keep learning, and keep building something that actually feels like yours.

Thanks for reading. Now go build something.