How to Avoid Seller’s Remorse

What you need to know before you sell your business

You’ve built your business from the ground up. Put in the late nights, built long-standing client relationships, and survived more than one market shake-up. Now you’re thinking about selling — maybe retirement’s on the cards, maybe life’s priorities are shifting, or maybe you’ve simply taken the business as far as you want to go.

Whatever the reason, selling your IT or telecoms business is one of the biggest decisions you’ll ever make — financially, emotionally, and personally. And while it can open the door to exciting new chapters, it can also leave owners with a nagging sense of regret if they’re not fully prepared.

Here’s what you need to know to avoid seller’s remorse — and sell on your own terms.

1. Know Why You’re Selling — And Be Honest About It

Clarity is everything. Are you looking to cash out and retire? Free yourself from day-to-day stress? Pivot into a different sector?

Being clear on your “why” helps you:

  • Set realistic goals for the sale
  • Choose the right buyer
  • Make peace with the decision emotionally

When owners aren’t sure what they want from the sale — beyond “I think it’s time” — regret creeps in later. Take time to reflect. Talk it through with someone you trust. This isn’t just a business decision. It’s personal.

2. Start Planning Earlier Than You Think

Many owners start the selling process too late — when they’re tired, burnt out, or reacting to external pressures like ill health or changing family circumstances.

The truth is: a well-planned exit takes time. Often 6–18 months from start to finish.

You’ll want to:

  • Get your finances in order
  • Identify areas to improve business value
  • Understand tax implications
  • Consider succession options (especially if staff or clients are like family)

Planning early gives you control. And that control makes a world of difference when the moment comes.

3. Work With Someone Who Understands Your Sector

Selling a specialist business like yours isn’t like selling a café or a retail shop. IT and telecoms buyers want specifics: customer contracts, recurring revenue, technical capabilities, supplier relationships, and more.

Working with a broker or advisor who understands the sector ensures:

  • Your business is properly valued
  • The right buyers are approached
  • You’re not pushed into a generic or underwhelming deal

The right advisor acts as your filter and your shield — and that alone helps prevent regret.

4. Think Beyond the Money

Of course, price matters. But seller’s remorse often stems from things money doesn’t solve.

Ask yourself:

  • Will your staff be looked after?
  • Will the buyer uphold your standards with clients?
  • Are you comfortable with how your brand will be used?
  • What will your day-to-day look like once you’re no longer involved?

Many owners feel lost when they sell. That’s normal. But it’s easier to move on when you’ve thought about what’s next and chosen a buyer that aligns with your values.

5. Give Yourself Time to Let Go

Selling isn’t an overnight emotional shift. It’s a process — and it deserves space.

If possible, phase yourself out gradually. Stay on as a consultant for a time. Hand over relationships properly. Say goodbye in a way that feels respectful and right.

This allows you to close the chapter with confidence rather than confusion.

In Summary

Selling your IT or telecoms business doesn’t have to end in regret — but it does require forethought. Know your reasons. Plan ahead. Surround yourself with the right people. Think about what matters beyond the money. And give yourself time to make peace with the change.

When you do all that? You’ll walk away proud of what you built — and excited for what comes next.

Thinking about selling your IT or telecoms business?
We specialise in helping owners like you navigate the process with clarity and confidence.
Let’s have a no-pressure conversation — and make sure you’re ready, not rushed.

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