Executive Summary
When you feel like quitting your MSP business, start by making the challenge smaller. Focus on the next useful action, prepare for the difficult conversations ahead and remind yourself why the business matters to you. A tough period needs attention, but it does not have to decide your whole future.
I nearly quit during my 422-mile cycling challenge to Glasgow. I have also faced business moments when walking away felt easier than carrying on. Four things helped me keep going: remembering that the immediate discomfort would change, preparing properly, breaking the target into smaller parts and having a cause worth fighting for.
For managed service provider owners and IT sales teams, those lessons can help when prospecting feels unrewarding, a sales target looks too big or confidence takes a knock. Here is how I apply them, with practical examples you can use in your own business.
Why does quitting feel easier when business gets tough
There have been plenty of times when quitting has felt easier than carrying on. Both in business and in life.
Like when, as a result of several mistakes on my side, I realised my business owed HMRC over £118,000. Or when I had a wage bill of £42,000 to pay and was £27,000 short with 2 days to go.
Then there was Kirkstone Pass.
During my cycling challenge in September 2026, I went around a corner and saw a 16% gradient hill that seemed to go on for miles. My legs hurt. My body hurt. Getting off the bike felt like a very attractive option.
If you run an MSP, you may recognise that feeling. You have put time into a proposal and the prospect has gone quiet. You have made calls, sent messages and still have an empty diary. Meanwhile, customers need support and your team needs answers.
At that point, stopping can feel like relief. But before you make a big decision in a difficult moment, give yourself something practical to work with. These are the four things I kept coming back to.
1. How do you get through a difficult moment without giving up
On that hill, I kept saying to myself, “Stay in the fight. Stay in the fight.”
I could not make the road flatter. I could make another rotation of the pedals. Then another. Eventually, the steepest part eased, I could see the top and I made it there.
The thought that helped was simple: this particular moment would not last forever. I did not have to feel comfortable to make a little more progress.
In sales, it is easy to let one difficult experience become a judgement about everything. A prospect rejects your proposal, and suddenly you are telling yourself that nobody wants what you offer. A call goes badly, and you decide you are rubbish at selling.
Pause and look at what actually happened. Did the buyer explain why they said no? Was there a genuine need? Had you agreed a next step? What can you learn before the next conversation?
For example, imagine an MSP owner loses a managed IT support opportunity because the buyer cannot leave their current contract for another year. The useful next action might be to agree a future review date and find out what would make a change worthwhile. That gives you something to act on instead of carrying the rejection into every other conversation.
You do not need to solve the whole sales problem this afternoon. You do need to choose the next useful step.
2. How does preparation improve confidence in MSP sales
I did not arrive at the start of the ride having done nothing. I trained in the rain, covered different distances and rode up hills. I also thought about the food I needed before getting on the bike.
Preparation did not make Kirkstone Pass easy. It gave me something to rely on when it became hard.
The same applies to selling IT services. If you avoid talking about money until the prospect asks for a proposal, that conversation is likely to feel uncomfortable. If you practise asking sensible budget questions, you become more familiar with the situation before a live opportunity depends on it.
Take a cybersecurity sales meeting. Before you join the call, think about the business problem you want to understand. What prompted the conversation? Who would be affected by an incident? How does the company decide which risks to address? Who needs to be involved in agreeing an investment?
Then practise saying the questions out loud. Ask a colleague to play the buyer. Get them to challenge you with, “We already have an IT company,” or, “That sounds expensive.” Listen to your response. Does it invite a useful conversation, or do you rush straight into defending your service?
The experts were once beginners. I would not have been able to ride for that long without practice, just as I would not have been able to have difficult sales conversations without practice.
Pick one part of your sales process that you keep avoiding. Prepare for it and practise it before your next meeting. If you are unsure what to do, ask for help.
3. How can you break a large sales target into manageable actions
422 miles seemed like a lot at the start. It was.
But the ride was split into 6 daily totals. Within each day, I broke the distance into smaller parts. On the second day, when we had 80 miles to cover, I thought about 4 lots of 20. Those became 4 lots of 5. In the toughest moments, I focused on 1 mile at a time.
That smaller target gave me somewhere to put my attention. Finish this mile. Take a breath. Go again.
You can do the same with a sales target. If you want 10 qualified meetings in a month, think about 5 blocks of 2. Then work out the actions you can take to create the next two conversations. The table below shows how I would translate the cycling lesson into an illustrative MSP sales plan.
Level | Cycling example | Illustrative MSP sales example |
Whole target | 80 miles in a day | 10 qualified meetings in a month |
Smaller milestone | 4 stretches of 20 miles | 5 blocks of 2 qualified meetings |
Immediate focus | The next 5 miles | Prepare outreach to a small group of suitable prospects |
Next action | Complete the next mile | Make the next relevant call and record the outcome |
Original framework based on my ride. Sales activities are examples, not guaranteed conversion rates.
You cannot control whether the next person agrees to a meeting. You can control whether you have chosen a suitable prospect, prepared a relevant reason to speak and followed through on an agreed action.
Track the response as well as the activity. If your message is not creating conversations, review it. If you are getting meetings with unsuitable businesses, review your targeting. Breaking down a goal should help you learn as you go.
For more on building that rhythm, read MSP Prospecting: Why Consistency Wins New Clients
4. Why does having a cause help you keep going
The most important factor for me was the reason behind the ride.
My cause was my late mum and Marie Curie, the charity that helped look after her during the last week of her life. Kim, the nurse, stayed up through the night to care for Mum, allowing our family some time to rest.
I wanted to repay the care that she and the organisation had given us. When the miles felt long and I wanted to stop, I thought about that.
You can read more about The work of Marie Curie Nurses and Healthcare Assistants
Kim had kept caring for Mum through the night. Remembering her commitment helped me make another effort when I was tired.
Within the Seven Figure model I use to guide MSP business owners, the first block in my 28 steps is Vision and Why. There is a reason for starting there. When the work becomes difficult, you need to remember what you are trying to build and why it matters.
For you, it might be providing for your family, creating a business that gives you more freedom or building a team you are proud of. It might be a personal ambition you have carried for years.
Be specific. “Grow the business” is a target. What would achieving it allow you to do? Who would benefit? Why would that matter enough to get you through an uncomfortable conversation or another morning of prospecting?
Write the answer down. Keep a reminder on your phone or somewhere you will see it before you start work. When the next difficult moment arrives, give yourself a reason to take the next step.
What should you do today if you feel like quitting
Start with the challenge in front of you. Write it down clearly. “Sales is not working” is too broad to act on. “We are not getting enough conversations with suitable prospects” gives you a starting point.
Choose a small action you can complete today. That might be practising your opening question, reviewing a stalled opportunity or following up with a prospect who asked you to get back in touch. Put time in the diary and do it.
Then review what happened. Get help with the part you do not understand. You can stay committed to the outcome while changing an approach that is not working.
I nearly quit. These four things helped me carry on, reach Glasgow and look back on a challenge I was glad I had finished.
What is your next mile?
If you run an MSP or IT services business and want help turning a difficult sales target into a practical plan, Explore sales mentoring with James White
Eat or be Eaten. You have a choice!
Frequently asked questions
How do I stay motivated when prospects keep saying no
Look for the reason behind the response. Review the suitability of the prospect, the problem you discussed and the next step you proposed. Choose one improvement to practise before your next conversation, so each setback gives you something useful.
What should I do when my MSP sales target feels impossible
Break it into smaller milestones, then identify the activity needed to work towards the next one. Use your own sales results to judge how much activity is realistic. Review both meeting quality and progress, rather than only counting calls or emails.
How can I prepare for a difficult sales conversation
Research the business, decide what you need to understand and practise your questions aloud. Rehearse the objection you are most worried about with a colleague. Focus on understanding the buyer before explaining your solution.
Does persistence mean continuing with a sales approach that is failing
No. Review the evidence and adjust your targeting, message or process when necessary. Staying committed to a goal includes learning from what is happening. It also means recognising when an individual opportunity is a poor fit.
How do I find a meaningful reason to grow my business
Ask what growth would make possible for you and the people who matter to you. Describe a specific outcome, such as supporting your family or creating more freedom in your week, and keep that reason visible when the daily work becomes difficult.
What will you do differently this week
My reward was riding into Glasgow and knowing Somerset to Scotland was complete. I am already thinking about what my next challenge might be.
Yours could be the testimonial request you have avoided. The introduction you have not asked for. The first step towards giving someone else responsibility for winning business.
What could happen if you took that action?
And where will your business be in a year if you keep putting it off?
Choose something that matters, decide when you will do it and follow through.
If you would like help turning your MSP’s growth ambitions into a practical sales plan, get in touch with me. Tell me what you want to change and the action you are ready to take.
