When Things Don’t Go According to Plan: Navigating Boundaries Between Business and Free Support for Friends

In life and business, things don’t always go as planned. Sometimes, the so-called "sure things" – or "dead certs" – turn out to be anything but certain. It’s a humbling reminder that even with the best intentions and careful planning, outcomes can be unpredictable.

One common challenge faced by business owners, entrepreneurs, and freelancers is navigating the delicate balance between helping friends for free and maintaining a sustainable business. Supporting those we care about can feel rewarding and meaningful – but where do we draw the line? After all, generosity won’t pay the bills or put food on the table for our families.

Why Helping Friends Feels Right – But Can Go Wrong

Helping friends, especially when they’re in need, feels like the right thing to do. But if we’re not careful, it can lead to blurred boundaries, unfulfilled promises, and even resentment. Whether you’re offering property-related advice, professional services, or lending a hand with creative projects, it’s important to ensure that your kindness doesn’t undermine your own livelihood.

Too often, small favours snowball into unpaid, time-consuming tasks – preventing you from dedicating that time to paid work or much-needed personal downtime. So, how can you protect your time and energy without feeling like you’re letting your friends down?

1. Be Clear from the Start

Honest communication is key. If a friend approaches you for help, be upfront about what you can offer for free and what you would typically charge for as part of your business. For example:

• "I’d love to help, but as this is quite time-consuming, I’ll need to charge my usual rate after the initial consultation."

• "I can offer some advice over coffee, but if you need something more in-depth, we’ll need to set up a formal arrangement."

This sets clear expectations and avoids misunderstandings further down the line.

2. Remember: Time is Money

Even if a task seems small, it still takes your time – and time is one of your most valuable resources. By undervaluing your own time, you’re effectively undervaluing your expertise. Helping out for free now and again might seem harmless, but consistent unpaid work can take a significant toll on both your income and personal wellbeing.

Ask yourself:

• Would I be willing to give this same amount of time to any client for free?

• If I continue working for free, will I be able to cover my financial obligations this month?

3. Offer Alternatives Instead of Free Work

If you don’t feel comfortable charging your usual rate for a friend’s request, consider offering a discounted service or pointing them in the direction of resources that can help. For instance:

• Share free online resources or industry tips that they can use independently.

• Offer a reduced package that doesn’t eat into your most valuable time or energy.

• Set clear boundaries, such as limiting your involvement to a quick review rather than taking on the entire project.

This way, you’re still providing value without overextending yourself.

4. Set a “Friendship vs Business” Policy

Having a mental or written “policy” about how you handle requests from friends and family can make life easier. Decide in advance:

• What types of support are you willing to offer for free?

• How much time are you prepared to give before compensation is expected?

• At what point do you transition from a casual favour to a formal agreement?

For example, you could commit to helping a friend for an hour but agree with yourself that anything beyond that requires compensation.

5. Don’t Be Afraid to Say No

Saying no doesn’t make you a bad friend – it makes you a responsible business owner. If taking on unpaid work jeopardises your business or personal commitments, it’s perfectly acceptable to set boundaries by saying no when needed. In fact, setting healthy boundaries can strengthen friendships because they’re based on mutual respect, not assumptions or unspoken expectations.

Try saying:

• "I’m really sorry, but I have a busy work schedule and can’t commit to this right now."

• "I wish I could, but I need to focus on paying projects to keep my business running."

True friends will understand your position and respect your honesty.

I’ll be honest – I know it’s much easier to say these things than to do them. I still find myself struggling with this at times. However, I’ve learned that every time I set a clear boundary, it strengthens both my business and my relationships. Saying no when necessary isn’t selfish – it’s a conscious decision that allows me to stay focused and present for the people who matter most.

Final Thoughts

There’s no shame in wanting to support your friends, but there’s also no shame in needing to protect your own business and financial security. It’s about striking a balance between generosity and sustainability.

By setting clear expectations, valuing your time, and knowing when to say no, you’ll not only build stronger friendships but also foster a thriving business. Remember: when you look after yourself and your livelihood, you’re in a better position to help others in the long run.

Boundaries aren’t barriers – they’re bridges that support fairness and mutual respect.