Coffee with Jennifer Holloway

Jennifer Holloway

Coach, Speaker and Author of Personal Branding for Brits

Age: Late 40s

Zoom Coffee

Describe your career path in two or three sentences including any twists or turns ending with where you are now.

If I had stayed on the career path that I was on when I left school at 16 I would be a graphic designer. But a couple of years into being a designer, I realised I could continue to be a decent designer, but I’d never be a great one. So I stepped back and thought what am I actually good at?

Yes, I was creative with images but I was actually much more creative with words and this led me into PR and media relations for the next 15 years. Again, although I was good at it, I never felt I was the best at it - that it came naturally to me.

Fifteen years into my PR career, I became clinically depressed and this led me to do a whole reassessment. During this time someone asked me, “If you could wave a magic wand and know whatever action you took would work out, what would you do?” and my instant reply was “I would jack my job in”. My response surprised me, but I did it, trained as a coach and then niched into personal brand coaching and training.

When I niched (which is one of my top tips for people wanting to reinvent their careers) by pinning down the very specific thing I did, my business took off.

How long did it take you to figure out that niche?

I started with executive coaching and it was probably a year in when, sitting down with a client after a session, he said to me, “You’ve turned your back on 15 years of communication experience and I don’t think you realise how much of that actually came into helping me. Your ability to put my own words in my mouth in a way that I could never come up with myself – that’s what you are really good at”.

It was that bit of feedback that got me thinking about how do I make this different and my own?

What decision / experience proved to be the most helpful to your career?

Feeling sure that I was on the right road. What I mean is ‘personal brand’ as a concept in the UK, when I started 12 year ago, was unknown. People were saying, ‘What the hell is it and why would I pay you money for it?’ (It’s a bit like when coaching started out; no one knew what coaching was but now every organisation embraces coaching.)

Even when that evidence was saying I was on the wrong road, I thought, ‘Nope, I am on the right road – it’s just a matter of time until other people (i.e. clients) catch up with me’.

I just had to wait, so sticking to my guns was the most helpful thing.

What advice would you give your 20 year old self knowing what you do now?

Don't listen to people saying, ‘You should be…[whatever they thought I should be doing]’. As I’ve got older, I’ve come to embrace the fact I am, as someone once described me, a lone wolf. But when you’re 20 and you don't know you're a lone wolf, you end up thinking: I should be going to parties, I should be hanging out with people, I should be going to the pub and getting drunk.

And years later you realise you shouldn’t have be doing those things because they weren’t you and never will be you. It’s not simply a case of ‘learn to be yourself’. It’s more a case of ‘learn more quickly who you are so you can embrace it’.

For me now, I can say I am a lone wolf and am proud of it, but I wish I’d known that when I was 20.

What do you think is the biggest challenge for people making a career re-entry or re-invention later in life?

It’s not so much knowing in our own minds what we have to offer, it’s more convincing others to think further than their preconceived notion and sell them what we have to offer. Often, someone starts off sure of what they are doing, but that surety gets chipped away because they’re finding it hard to convince people.

So, I think the biggest challenge is convincing others that just because you are not the exact shaped peg to fill the shape of the hole they have, maybe they need to look at this in a different way and change the shape of the hole – because you are bringing stuff that they hadn’t even thought about.

And that’s where understanding your story and personal brand is so important?

Absolutely, because how are you going to sell it to someone if you don’t even know what it is?

What are the opportunities for people wanting to reinvent or restart their career later in life?

The opportunity is selling the value of having been around the track a few times.

Here is a perfect example. I had a client who is in her mid-40s with a long career in event management. She was recently made redundant and I was working with her to develop her personal brand. She was worried that with so many younger people on the event scene nobody was going to listen to her because she was older and therefore seen as out of touch.

And my mouth fell open. “What do you mean!?” So I reminded her of the little black book she’d talked about.

I said, “How are you not selling that? You should be saying: Well the youngsters might have all the ideas, but I have the trusted contacts and there is not a single problem that could happen that I wouldn’t have somebody on speed dial to fix it”.

You have to sell the fact that you have been around the track.

Why do you think creating a personal brand is so important especially for people wanting to enter their third or second career act?

If we consider your brand as comprising who you are and what you are offering, then it is a case of sitting down and really thinking about your offering with clarity and precision.

You can say, ’Oh I am somebody who is good at strategic thinking’. But what does that even mean?

Instead, if you said, ‘I am somebody who is really good at seeing around corners – and the next corner, and the next corner, so what I can do for you is…’ This is so much more engaging. So having clarity and confidence are the first things.

The other thing is to stay focused on the key points - you don’t want to be a jack of all trades. Especially when we need to pay the bills, it is easy to think, ‘If I am too specific about what I offer, I will close myself off from potential customers and narrow the number of people who would want to buy from me’. It feels counter intuitive.

But by narrowing your audience, you can then focus on those people who will best understand what you do and benefit the most.

I always say you need to give people a tiny box in which to put you in their minds, so when the time is right and they are talking to somebody else they can very quickly pick up that box and pass it on to the next person. But if you try and give them this huge, huge crate with everything you could possibly do in it, it’s too much to remember and they won’t find it as easy to pass it on.

I liken it to Mary Poppins: you need to walk through that door with a single carpet bag – one thing you’re known for. Then, once you have established a relationship with the person and they know you for that one thing, you can open up that bag and say, ‘I can also offer you a hat stand and a mirror and a parrot in a cage’.

But don’t try and walk through the door with all of that in your arms at the same time. The brain can’t compute. You think niching will shut you off from business, but being too general does.

What is your top tip for people thinking about re-inventing their careers?

A lot of people say you need to ‘Find your passion!’ which is a word I hate, because it’s become so overused and bland – plus what is someone meant to do with that? How would you go about finding your passion?

Instead, the practical thing to do is to think about your drivers. Your drivers are what motivate you and make you happy, so if you base your new career on those, you’ve more chance of staying motivated and happy.

One way to work them out is by looking back through your previous career and figuring out what makes you happy, keeps you satisfied and gives you a sense of pride. For example, go back to the very first job you ever did (for me it was working in a sandwich shop on a Saturday) and visualise yourself there. Then visualise yourself in the next job and the next job, etc and create a mental film of your career – all the way to the present day.

Then play it back from the beginning on fast forward, stopping at the points in your film where you loved going to work – that you actually looked forward to walking through that door. (It is never a whole job, it’s always a moment within a job.) Those are your drivers. Then do the same again but stop at the points in your film that you hated going to work – when you had to talk yourself through the door. Those are the opposite of your drivers.

Next, dig into the details, thinking of the components that made up each situation in order to come up with a checklist of what drivers have to be met for you to be happy. (You can do the same with thinking about when you were least happy, to create a checklist of what to avoid.) Be specific: don’t just think, ‘I like leading people’. Think about the optimum number of people you like to lead, what sort of level of experience they have, how you like to lead them, what you like to get out of leading them…and so on.

Recommendation: Favourite book to read, website to browse or podcast to listen while sipping coffee?

My favourite book that I return to time and again is Barrel Fever by David Sedaris. I read it when it first came out and hadn’t laughed out loud so much at a book for a very long time.

For a much shorter read I get The Week and work my way through it in short bursts whenever I put my feet up for five minutes.

Since lock-down, I’ve become a fan of Instagram (to look, never to post) and follow an eclectic mix of musicians, wildlife photographers, cake decorators, hairdressers, drag queens and anyone posting funny photos of dogs.

My podcast tastes change monthly and can I go from being a huge fan to suddenly not bothering to listen any more. My current favourite is The Treehouse with Danny Baker. It’s essentially him setting out random topics for members of the public to email in with their real-life stories, which are often hilarious and stranger than fiction.