Freelancing: The grind behind the success
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Freelancing: The grind behind the success

Freelancing. The seeming holy grail of today's work/life balance paradigm - the new American Dream. Workers galore are joining The Great Resignation turning into freelancers.

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Are they (we) right? Who knows? A business leader in Heineken I appreciate very much said in his parting address: "There are no right or wrong decisions, there are only decisions, and we have to make those decisions right". I find this view quite liberating and encouraging. So now that you/I have made the decision, it is up to us to make it right.

How to become a successful freelancer?

Everyone has a different definition of success. Some of us want to make millions of billions of dollars and euros, some of us want a steady income stream to pay for the day to day and measure our success in the time we have for our families, our friends and doing other things we love.

This article isn't a success formula to becoming a successful freelancer as I am too on the journey to "freelancing sustainably".

The aim of this article is to share the pain, and share some directions that I hope are working for me and will hopefully work out for you. The problem with information that is available to us today in all media outlets is that we are only being fed the multimillion dollar successes, but no one really talks about the grind.

1. Be resilient for the grind

If I was to isolate one single trait of every single successful freelancer or entrepreneur (because we are entrepreneurs - I think the popular term is "solopreneur", which just goes to show that we too are full of keyword BS...) it is: RESILIENCE.

You have to eat resilience for breakfast, lunch and dinner, and before going to sleep brush your teeth with it.

Quotes are popular, so here is one that I find particularly relevant and to which I go back to often when I am feeling down:

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So if there is one tattoo you should get as a freelancer this is the one:

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Here is my own experience from yesterday: after careful preparation for a sales meeting of a product I absolutely love to do I was told within minutes of the meeting ending by the prospect that they weren't interested in it for the time being. Better make sure you can take hits in the face like a boxing champion.

I won't give up on the prospect mentioned above, it is just business, we will be working most likely on other avenues of common business and that person is a very appreciated member of my network and whom I have a high regard of. If not today, the opportunity will come tomorrow. Never burn bridges.

2. Do what you are really good at, and make sure it is something you love

Yesterday I saw an interview with Steve Jobs on YouTube about passion for business and he said that we better make sure that we do something that we love, because we have to have the resilience to go back to it day in, day out, even when things aren't working out - if it's a job we won't get there, if it's an obsession then we just might.

I wrote an article a while ago on how to isolate what we are good at. It can be found here.

3. Cast a wide net

Landing assignments is a numbers game initially. Why? When you are starting out people might know of you in your industry, however there is only so much work to go around for freelancers in your own network.

You believe you are the best at what you do, and you should as this will give you the strength to sell yourself. Self-belief is key to self-selling. All that being said many potential target clients will deem that they can do what you offer with their own resources and few will see the reason to engage you.

Below is an overview of my "hit list" in the last eight months. As you can see not all the lines go to the end, in fact a scarily large proportion are finishing early in the process with red, and many are in still in development.

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4. Prepare for long sales cycles and cash in as soon as possible

In my tender days of being a sales rep in Carlsberg I was told by an experienced colleague: "Until you've been paid for it it's free."

It was funny to my 24-year-old self as my salary was being paid every month. Not so funny to my 39-year-old self when my salary is the minimal allowed by the law and you are living from that dividend payout at the end of the year.

Sales cycles tend to be extremely long. If you plan on being paid at the end of the cycle make sure you have the liquidity to navigate the time needed. Or, better, get the client to agree to pay a certain amount upfront. This will create two things:

  1. You will have cash to run on for the duration of the project
  2. It will create commitment by the client to the project as they've already paid for part of it upfront

There is a book I can recommend on the approach to business as a freelancer:

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I have no affiliation whatsoever with the author or publisher, I am just sharing what helped me and hopefully it helps you. And this is also a way of saying thank you to the author for providing much needed advice (in a book that I paid for. Now this is freelancing mastery: creating content that people are willing to pay for and also recommend it to others - that makes a successful and impactful product. Learn from the best quickly and apply to yourself).

5. Network, network, network...

The most cost effective and efficient way to push your services is via your own network. A network is like a house plant, you have to water it, you have to trim it and you have to take care of it. Make sure you maintain constant contact, don't be greedy, help others, and they will help you.

6. Always be ready

Don't be too pushy and hard selling, but also never be shy to offer yourself when the opportunity arises.

Quote time (Ancient Greece this time!):

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Like a big cat, always be ready to pounce, but be smooth before and be decisive in the moment. Like a big cat however you will also often go back to your lair hungry.

Here is an example of it from something that happened to me:

I was interviewing for a marketing director role with a reputable company in the country where I reside. I made all the rounds of interviews and the next meeting was intended to agree on terms and conditions - what could go wrong, right? Well it turns out on the evening before the meeting (at 11PM!) I received an email that the company had decided not to hire anyone for the role.

If I wasn't sitting down at the time of reading the email I would be falling down...

What did I do? First I was furious, then I calmed down, went to bed, couldn't sleep. I woke up at 3 AM, wrote back an email thanking them for the opportunity and sent them my company sales deck with the services I had on offer. I scheduled it for 7AM the next day (I was thinking: if they can send me emails at 11PM I can send them emails at 7AM :P).

I received a call from the CEO of the company that morning to come in for a discussion for a project brief.

In the end the project didn't materialise for whatever reason but the point is I was ready to pounce, not taking no for an answer and taking the fight to round two. A no isn't always the end of the road, you have to learn how to navigate it and maybe the opportunity will be just around the next corner.

7. Manage your impatience

Your prospects are more important to you than you are to them, at least initially until the moment you start being so invaluable to them or the market that you get to pick, chose and charge.

Allow for time between contacts. If you are too impatient you might come to be perceived as overly aggressive. Be steadfast, be measured.


So here it is, a longer Saturday read, hopefully you enjoyed it, hopefully it will help you. Drop a line in the comments to share your own experience!

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