Once upon a time I thought asking for help was a sign of weakness. Starting my career, I always wished I was older so that I had more experience; I wanted to seem credible to the companies I was talking to – particularly when I was speaking to managers and directors of well-established businesses.

I went with the strategy of ‘always say yes and then figure out how to do it later’. Which, yes, does work…to a point.

But the trouble is, that if you’re constantly saying ‘yes’ to stuff you know nothing about, you’re constantly fighting to keep up. Regularly working into the small hours to upskill in various marketing techniques I felt constantly stressed, which did nothing for my physical and mental wellbeing. And it meant I was dabbling in everything but failing to master anything.

It all changed when…

Turning freelance, one of the first clients I worked with (an agency) asked me to interview someone to produce some editorial to help promote an event they were speaking at.

Listening to her speak blew my mind.

The woman in question had successfully climbed the corporate ladder, achieving amazing things in such a short space of time. And her secret…


Every time she encountered a challenge, she would look for someone who could impart their wisdom to move her forward. And successfully engaging a mentor was really simple…

Just ask. In her words:

“Most people are flattered you’ve asked, and more than happy to help you.”

The concept felt alien. But as someone who tries to live in a space just outside of my comfort zone, I thought I’d try it.

My first experience of mentoring

At the time, I had just started freelancing and had a newborn son. Life felt overwhelming to put it nicely. So I sought out a mentor to help me navigate the challenging world of achieving the work-life balance.

I turned to someone in my personal network who I had worked with previously. She too had started a business (an agency) and grown it alongside being a wife and mother, and generally appeared to be winning at life.

It was the first time I’d ever really asked for help. And to be told, “Yes! I’d love to meet for a coffee” felt wonderful.

I remember walking into Costa feeling completely nervous and all my words seemed to come out jumbled. But after some cake and general chit-chat, I managed to articulate my struggles, and received some great advice:

  • Focus on ‘quality’ time over ‘quantity’ time
  • Only do the things you’re really passionate about
  • You can’t do everything – so outsource (mainly the dreaded housework!)
  • Make time for yourself (although I’m still rubbish at this)

Incorporating mentoring into business-as-usual

Since that first experience it completely changed my outlook on mentoring. Now, whenever life gets tough (personally or professionally) I find someone who I think could help me and invite them for coffee and cake. And people are always more than happy to help.

Some of the challenges I’ve enlisted mentors for have been:

  • Creating new service offerings
  • Whether to take on certain opportunities
  • Pricing
  • Professionalising my business
  • Sales

Choosing a mentor

Possibly the most important aspect of engaging a mentor is selecting the right person. Yes, your friends and family are great to turn to when you need some advice/comfort, but have they felt how imposter syndrome can be all consuming? Have they figured out how to unblock a sales pipeline? Have they set up a business, and then juggled it with the 101 other commitments in their life?

Probably not.

The thing about a mentor is that they can completely empathise with your situation and know exactly how you’re feeling because they’ve been there.

And most importantly…

They got out of that place. And that’s the insight you want. You want to know the things they’ve tried, what worked, what didn’t – and why. What they’d advise in your situation.

You want someone who’s going to really listen to your challenge, and understands the context so they know how to move you past the issue.

When I recently turned to a mentor for help with sales, he would never claim to be any kind of expert. He’s not written a book. You won’t find him up on stage working the conference circuit. And his name isn’t listed on some top 10 leader board of the best sales people of all time.

When I needed help, I found someone who knew me, and therefore knew how comfortable I’d be doing/saying certain things during a sales meeting…

I found someone who has a breadth of sales experience, working with both SMEs and enterprise. Who has experienced times of success, where they’re bringing in thousands (if not millions) in revenue. But most importantly, they’ve experienced the tough times, when the pipeline dries up, when opportunities get stuck – when prospects are making all the right noises but refuse to sign on the dotted line.

Approaching your chosen mentor

Possibly the scariest part of mentoring is asking for help. For me, admitting that I’m struggling is tough because I’ve always had an attitude of ‘power through’.

The mentors I’ve selected in the past are all people I know personally. Perhaps it makes it slightly easier as I can invite them out for coffee and a cake.

But if I didn’t know anyone personally who could help, I’m pretty certain I know someone who has a connection. In which case, my method would be the same – invite them for coffee and cake, and ask if they can make an introduction.

Asking for help has always felt inherently tough, but the reality is that most people are kind, and they genuinely want to see you succeed. Certainly, a lot of the people I know believe more in me than I do, and they will go out of their way to support me if they know I’m struggling.

So just ask – I promise, you’ll be surprised by the response.

Give your mentor feedback

I may have treated my mentors to coffee and cake*, but is it enough?

I’ve always thought that if someone asked me to help, I’d want to know how they were getting on (and to see if my advice was actually any good!). So after we’ve met, I always message my mentors to let them know what I’ve done off the back of their advice. And then follow up when I can share the outcome with them.

* strictly speaking this isn’t true. I’ve had a couple of occasions recently where my chosen mentors** have actually treated me to the cake!

** turns out sales people can be genuinely nice, and not the slimy/lying/cheating stereotype they’re made out to be!!

What next?

As with most things in life, business challenges are cyclical, which means as one ends another will shortly begin.

The important thing is to know your limits – know what you’re capable and comfortable coping with, and if/when you may need to enlist the specialist help of a mentor.

And for every challenge you face, you should ask yourself who you know that is best placed to help – rather than relying on the same person for advice every time.

The best advice I can give you is to prioritise growing your network – and not just within your creative discipline – because you never know what sort of help you’re going to need.

Are we connected?

With so many social platforms I find I’m struggling to keep up with who I’m connected to on each one. So if we’re not already…

Connect with me on LinkedIn