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The Hustler’s Tool Kit - "How to survive as a first-time freelancer"

So, as a big-time planner, you have suddenly found yourself independent, solo, freelance, free as a bird (or laid off, unemployed, let go and chucked out of the nest, just to bracket off some other ways of describing the situation).

Suddenly you are responsible for bringing in the clients, the work and indeed the money. Because, to answer Marvin Gaye’s plaintive query about “what’s going on?”, suddenly, ain’t nothing going on but the rent.

In the past you have had the new business team, the account handlers, the suits, the lunch machines to bring in the work. For sure you did your bit on the pitches, and the clients always loved working with you. But now, that sharp, messy (grubby?) end of the business is where you need to be.

Like it or not it is time to start hustling.


This may fill you with horror. It did me.

So to re-assure, I not asking you to turn yourself into a cold calling ice maiden, a conference networker of smarm and charm, or a hard bitten sales closer who always gets the contract signed (although you can do any of those things if you want. But I would guess that these are not really your style, if you are a planner).

But you do need to hustle.

Because this is about doing stuff. Doing stuff you may never done before. And doing a lot of this new stuff – persistently - because sales is a numbers game.


To orientate you, this will require action not thought.

I make this distinction because as a planner you will be good at thinking, inventing stuff, analysing things. And in your perilous circumstance, it is tempting to spend time agonising over your personal brand essence, fine tuning your products and services to the nth degree, analysing what you can uniquely offer the world (tomorrow…).

All the above, I am sure will do well, because you are clever. But, my fellow planners, that is the easy bit.

For sure, strategizing your new life will feel like “Work” and that will soothe you in these new, edgier times. But the hard truth is that the tougher task is getting out there and hustling in the market; to get “out and about” as a wise man once said to me (or “ait and abait” as he put it. He was dead posh and if even the posh people have to hustle then I reckon us middle class, semi-intellectuals can hack it too…)

So, as one who has been there before, let me make it all a bit smoother for you with eleven tools that will help very clever but mildly introverted freelance planners take their brilliance to market. And put food on the table.

1. The Big Pad

2. The Excel lists

3. The Percentages

4. The Edge

5. The iphone

6. The Shoes

7. The Ears

8. The Headlines

9. The Heart

10. The Books

11. The Door Handle

1. The Big Pad. Go into an arts and craft store and buy a flip chart sized pad (A2) with good quality paper and plonk it on your kitchen table/work top. Furthermore, leave it there for the next month or so despite what the family says. (BTW do this on paper, don’t be digital. I do not mean iPads. I mean art pads.

This white expanse is where you are going to scribble random lists, capture new thoughts as they occur to you, pen half-baked mind maps, note brilliant new ways of describing your offer; all the stuff that will be swirling around your head, all of the time.

The Hustle will be - needs to be - something that is always in your mind, at least for the first few months of this new era. So rather than try to keep them in mind until you are next “at your desk” you need a place to catch those thoughts. Hence in a “high traffic/high linger” zone like the kitchen.

Doing this will not only stop you from losing your thoughts, it will also make sure you retain your sanity. It is a whole new world you are braving and you do not want your brain whizzing around more than your fragile psyche can cope with. So have a place in the heart of your home where you “brain dump”, partly for your own sake but also for the rest of the family (you may need to explain why it’s there and not “on your desktop”).

2. The Excel lists. Pretty obviously you are going to be generating a list of prospective clients, useful contacts, or people it seems right to catch up with. I have experimented over the year and I don’t think you need a fancy data base system as such, but it is worth switching from paper to a spread sheet at this point My system is pretty crude and consists of about four columns. On the far right is the longest list and that is where I capture all the random people I want to catch/meet up with. Sometimes I add a note (or colour code) on whether I have emailed them, or seen them recently, as a simple reminder.

Then one to the left is a column that tends to be about a third the size of the previous one and is labelled “prospects” or “people who seem to want to work with me”. These are all the people who you have spoken to and, however vaguely, indicated that there might be something you can do for them. These are people you are going to follow up with, of course. Again, leave a note in the file.

Then, one more to the left, is an even shorter list of people who “definitely” want to work with you, or that you have supplied with a costed, written proposal. Obviously, you will be trying to close the deal on these with patience and charm.

Then the final column on the left will (eventually) be the people who are actually paying you money right now. In time this list will grow; that’s what the hustle does because, as I said, selling is a numbers game.

So “work” becomes working across the columns from left to right on a persistent basis:

1. servicing the existing clients

2. (also) following up on your proposals

3. (also) finding a reason to have a second meeting with those interested in you

4. (and also) arranging more meetings from the long list.

5. (and always) seeking to add new names to the long list, however marginal they may seem at the time.

Previously it was your job to do just item one and maybe contributing to some of the proposals (even if others did the chasing); now you need to do all five of the tasks.


But if you keep cranking the handle (or filling the sales funnel, if you squint sideways) then money will eventually flow. Or at least it seems to work for me.

3. The Percentages. One of the things that will keep you sane (but also motivated) is to realise that there might be only about a 33% conversion ratio at each stage. So, if you talk to 150 people, 50 might express an interest in working with you, about 15 or so might say they “definitely” want to do something and 5 will actually end up paying you on a regular basis.

Please don’t judge people who never call you back, after having seemed 100% on for it. Things change all the time and most people hate to say “no” when they can just leave it hanging.

But the main point here is don’t get too cocky when you have a stack of hot prospects. Probably less than half will convert and there is little you can do about that (or it might just be me; please report back with what you find…).

But what you can do is keep working the whole pipeline i.e. find something to seduce the “maybe there’s something” people and also ping an email to those “haven’t seen them for years” people that you scrawled down on the big pad last night.

Play the percentages and don’t take it personally.

4. The Edge. I mean this not in the sense of having the edge in sales technique but a simple mechanism of exploring the edge of your network. So rather than meet up with the people who you are most familiar with and similar to (i.e. other planners), go and talk to people who are very different to you and move in different circles. For example, if you have school age kids, arrange a work-time coffee with the other parents as they may open new doors to you.

The reason this works is that most “jobs” come from second or third order effects (i.e. they know someone who knows someone). Conversely, if you just go around talking to other planners, they will probably only know about the same jobs as each other, so you are limiting your reach. The technique is to explore the edge, even if you can’t immediately see what’s out there. Indeed, that’s the reason to go to the edge, to see further and find the unexpected treasures.

Some people call this making your own luck. But it’s part of a system. It’s not luck.

5. The iPhone. However, you like to contact people there comes the moment of truth when you have to go for it and quite possibly be rejected. My advice here – apart from cranking your lists as above – is that when you settle down to make contact, choose the people you really like first and only once you are in the swing of making phone calls (or writing breezy emails) then shift into the calls that, for whatever reason, you feel less good about i.e. work down the list starting at the fun end first.

There is a school of chore management that says you should get one of the tough jobs done first. My experience is that for this more intimate task (you are selling yourself, right?) start with people you really like - and indeed like you - and surf off that positive energy to keep working down the list. The morning will fly by.

I have to be honest, it’s tough doing this bit, so make it easy on yourself when you start, and then you’ll be surprised what you are capable of as you get into it.

6. The Shoes. I can’t be dealing with trying to adapt all of this for WFH, at least for now, but I am a great believer in going to see people for a coffee. Maybe at their offices, maybe at a coffee shop nearby, but I do believe in the power of the one to one chat.

As explained above, the hustle is a numbers game which can seem intimidating or a bit too close to becoming a ghastly salesperson. But if you frame it as just sitting down with a 100 or so people you already like - or are curious about - then that should seem like a much more enjoyable thing to do.

But you do need to stop “thinking”, put your new shoes on and suddenly everything’s going to be all right.…

7. The Ears. There are many books you could read about “selling” but as a planner you probably don’t need to do that. So relax, and do what you are good at: listen to them talk (you remember group discussions, you remember client briefings, it’s just that…). You may be anxious about “selling something”, especially in your new circumstance, but just do what you always do, ask good questions and try to undercover the need.

One tip, if you are in more of “sales” context, very often the client will rapidly ask you what you have to offer. Try to deflect that by saying something like “I will tell you about that in a moment, but first, can I hear a bit more about your business and the issues you are facing so I end up talking about the right part of my offer?”.

If this goes well, you may get to a rather pleasant feeling of them pulling your offer out from you, and you may indeed witness them persuading themselves that you are the solution to one of their most pressing problems.

Hopefully this will happen. And do remember to follow up promptly if it does (maybe moving this prospect one column to the left, in your record keeping). But match your enthusiasm with a pragmatic eye on the percentages. You may need three great meetings to get one actual sale.

8. The Headlines. Coming back to these meetings, having listened hard, it is also useful to have some headlines of what you have to offer. You should have pre-prepared this and rather than having a power point or long CV I have often found that “the rule of three” is worth bearing in mind (I mean this literally; have the three things cued up in your mind and then bring the right one of the three forward as the opportunity presents).

So, if you are offering yourself up as a planner what are the three projects that might best showcase your skills? If you are offering a training or new consultancy service what are the (snappy) titles of three services, you have to offer?

Then, assuming you have been listening hard to the client’s problem/need you can say, as if telling an anecdote, “that’s interesting because just recently I was working on a similar sort of project that was about XYZ that sounds a bit like your thing…?”. If you have picked well, they will start to quiz you thoroughly to find out if they want to buy some of that juicy XYZ from you i.e. you’re not selling any more; they are trying to work out how they can buy you…

9. The Heart. Often, and certainly with people who are more like friends/colleagues than commercial prospects/clients, it will become clear that no money is going to be earnt as a result of this conversation.

Having learnt from people much better at this game than me, the key thing is to be helpful to that person. Either in the moment, or by making an introduction, or following up with a book or link or whatever would be useful to them.

I have come to see “networking” as not a thing that happens with strangers over drinks on the edge of conferences but rather about a bunch of people all helping each other in any way they can. It’s not about “building a network” but about giving freely of what you can, to a bunch of people you care about, so one day good karma will happen to you.

So, with a good heart, whenever you can add some value to the network and the network will almost certainly help you back.

10. The Books. There will be times, perhaps many times, when you have hustled, chased, coffee’d and listened as much as you humanly can. In which case “sharpen the saw”. The reason you are already an amazing planner is that you have read (or written) all those books. So don’t neglect this. Become a good hustler, but also make sure you have something worth selling. Relax, read and write.

11. The Door Handle. But the best tool of all is the inside handle of your front door. Use it a lot, and when combined with all the other tools above, you will enjoy a whole new way of being a planner. At first “hustling”, as I have provocatively labelled it, can seem odd for a planner but, to quote the 1995 PlayStation ad, you too can lead a double life:

For years, I've lived a double life.

In the day, I do my job,

Ride the bus, roll up my sleeves with the hoi-polloi.

But at night, I live a life of exhilaration,

Of missed heartbeats and adrenalin.

And, if the truth be known,

A life of dubious virtue.

I won't deny I've been engaged in violence, even indulged in it.

I've assailed adversaries, and not merely in self-defence.

I've exhibited disregard for life, limb and property,

And savoured every moment.

You may not think it, to look of me,

But I have commanded armies and conquered worlds.

And though in achieving these things I've set morality aside

I have no regrets.

For though I've led a double life,

At least I can say…

I have lived.

Do not underestimate the power of Planners.

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