The Born Freelancer on Playing the Long Game


This series of posts by the Born Freelancer shares personal experiences and thoughts on issues relevant to freelancers. Have something to add to the conversation? Your input is welcome in the comments.


A freelance colleague of mine recently told me that he was sitting on what might be the biggest story of his career. So, I asked, why had he not gone public with it? “I can’t” he replied with a slight sigh, “I’m playing the long game”. Immediately I understood what he meant and respected him even more for his decision. It’s not an easy choice to make nor is it one that everyone would have the aptitude to play. But in the long term, for the working freelancer, playing the long game will almost always result in a greater volume of work as a result of an enhanced professional reputation.


The long and the short of it

I’ve always been a firm believer in playing the long game whenever possible. (There are always valid exceptions, of course). I’ll try to relate it to dealing with both potential employers as well as confidential story sources in this article but it always applies to both.

The short game is a gig you get, you do it, you’re done and that’s all there is to it. We used to call them “quick and dirties”. They are good to have to keep things interesting and to keep a steady flow of unexpected cheques coming your way. But they can take a lot of time to pursue and there is no way to guarantee their recurrence. In terms of simple cost analysis, they are short term gain only and as such, not the most productive use of your time and resources.

The long game is about establishing a relationship with a prospective employer. They get to know you. You get to know them. Work may come up from time to time. They get to know they can trust you to deliver. You get to know you can trust them to treat you well or well enough. In terms of cost analysis, while you might have to be patient you are looking at recurring long term gain.

In terms of pursuing a story, playing the short game might involve breaking a story first but at potentially enormous cost. That cost might involve lack of accuracy, or the betraying of trust. That approach may suit those in pursuit of headlines and fickle celebrity status but in terms of long term freelance career benefits the advantages are dubious.

In terms of pursuing a story, playing the long game is all about establishing your credibility with a source. It is about getting to know them as people and getting to know their story in depth. It is about respecting their wishes, their concerns, their point of view. It’s also about them getting to know you so they can relate to you more openly and freely.

In today’s world of instant-this and instant-that as well as the immediacy of social media, the long game may be seen by some as increasingly irrelevant or even as completely counter-productive. I would humbly beg to differ. You may not always choose to play it but when you do you should play the long game well. Here’s why…


First and foremost, playing the long game is about building trust.

By sitting on a story when requested by a source, for example, you may gain their trust. This could result in a steady stream of stories in future and a further expansion of your network of contacts when your source chooses to vouch for you with other story sources.

To be clear: This is not about cover ups or censorship or control of the press. In terms of trust it is ultimately about recognizing the impact going public can have on a story’s sources, respecting their wishes and judging the optimal timing accordingly.

Playing the long game will eventually benefit you professionally. Establishing trust, and thereby  expanding your circle of contacts, will inevitably result in more and more work. It is the difference between a job and a career. In the short game, you are going for the immediate bang without thought for anything further. In the long game, you are planning for your future, your career, and planting the seeds for a successful working life. Playing the long game means you will eventually write more stories and better stories, with greater depth and insights than playing the short game usually will allow.

Immediately after the bombing at Pearl Harbor, the great American broadcaster-journalist Edward R. Murrow is said to have had an informal conversation at the White House in which President Roosevelt revealed the true extent of the attack’s damage in an off-the-cuff remark. This was before he judged it appropriate to tell the public. Murrow had to wrestle with the story – was he told it “off the record”? The President had not made that clear. Murrow chose to play the long game and sat on the story. It all came out soon enough from many other sources. But Murrow felt it would have been a betrayal of trust with his source and perhaps even detrimental to the country unprepared for such news. So he missed one scoop. Playing the long game did no harm to his career, in fact it probably helped it. Just search for his name if you don’t already know about him!

In terms of an employer, the greatest single asset we freelancers can generate is trust. Trust that we can do the job. Trust that we will do it well. Trust that we will do it on time. You can only establish trust by playing the long game. Employers may be naturally wary of freelancers. Some see us as a necessary evil but as essentially unreliable. Play the long game and prove them wrong.



Playing the long game is all about establishing and building relationships. Without them a freelancer is isolated, totally and utterly. Today they may be called “contacts” or “networks” or “sources” but they are all relationships. In smaller niche social communities, where there may be an overabundance of freelancers competing for the same story, the freelancer who has taken the time to create relationships will come out the winner.

In the freelance job market, relationships mean the difference between getting work and not. Given the choice of two freelancers, one known and the other unknown, guess which one most employers will opt to hire?



Playing the long game will help establish your reputation.

A freelancer’s reputation or brand is paramount. Word gets around quickly amongst sources and potential sources, especially in niche areas of reportage (such as business news, health news, travel news, etc.) about whether or not a reporter can be trusted to convey a story well.

And employers talk to each other too! Don’t think they don’t just because they are competitors. Your reputation will precede you at every step of your career. Let it be a door opener not a wallet-closer.

Playing the long game will establish you as a committed career-savvy professional with long term credibility.



Playing the long game can increase your knowledge of a story or an area of expertise. It gives you time to research, one of the greatest deficiencies in today’s instant headlines. Rushing in to get the story first may result in revealing the gaps in your knowledge of a particular story or topic of interest.

And so one of the greatest advantages of playing the long game versus the short game is added accuracy. I know we live in an area wherein being the “first” is seemingly so prized. But ask those celebrities inaccurately reported as dead via Twitter about how they feel about today’s journalism. Don’t think they were too impressed. Nor were the rest of us. Playing the long game means to take the necessary time to absolutely, positively get the facts right.



Playing the long game means focusing on the longer term. It can help you evolve a better perspective on a story, on a job, and even on your own life. Rushing into things and playing the short game can have its merits too (like immediate cash), we’ve all done it, but it will never allow you the luxury of perspective with which to see things in their true historical context.



It is very easy to become cynical when reporting the day to day events of human beings. There is so much that goes on to become jaded about! But when dealing with sources I always try to remember that they are first and foremost fellow travelers in this crazy, mixed-up ride we call life. I try to treat them how I would wish to be treated if circumstances were flipped. Playing the long game facilitates this process. I would posit that there is a higher ethical commitment to honour beyond just getting the story first. What I mean by that is how we get the story and then what we do with it and how we treat the people who helped us along the way. Of course not everyone will agree which is probably why journalists rank so low on the respect and trust scale of most average people.


And how do I play the long game?

Like my colleague, it may mean temporarily sitting on a story when requested until the participants are ready to go public. They may turn to you as a confidant in the meantime, someone with whom they can share aspects of the story that no one else will ever access which you may use when the time is right.

With employers, it may mean not “blowing them off” simply because they don’t hire you for a specific gig.

So what it comes down to is that you should simply keep in touch. Whether there is an immediate story or job for you or not and especially when there isn’t.

In fact, when you have downtime, that is one of the best uses of your free time as a freelancer. Go through your list of folk you formerly worked for or who you have approached so far with no success but with whom you have established a good rapport. Follow up with them. Phone them, e mail them, use all the social media platforms you can. Let them know what you have been doing lately, what new skills you may have acquired, what you see yourself doing to help them solve their current creative problems in the near future. Needless to say – research, research, research their current situation beforehand. I will write more about what to say in a successful long game email in a future post.

(You can treat story sources in a similar way. Follow up with them, find out how they are doing, what they are up to, what developments have occurred in their lives/work since your last contact. You never know where it may lead).

In some cases you may even be able to set up face time. Coffee or lunch. An after work drink. Whatever. If they don’t feel pressured by you and can just enjoy your company it is an opportunity to network and reconnect like no other. It is also a vote of supreme confidence in your standing as a freelancer. You both know while there may be nothing for you today, tomorrow they may need your services. It works for both of you. Remember to ask them about their work, how it is going for them. Not only does it increase the professional and personal level of mutuality (hey, it’s called being polite!) it’s also helpful for any future pitches.

Who knows, they may have some inside information to help you with other contacts. Or they may want to use you as an informal outside sounding board for their ideas – something that could lead to work if their ideas pan out. And even if there is no work, you have at least renewed a potentially valuable contact. Remember – in future – if an employer has two or more freelancers equally talented to choose from and can only hire one – well, wouldn’t you choose the one who acted most professionally and you consequently got along with best?


The takeaway

Playing the long game with employers is a no-brainer. I don’t think there can be much to argue with on that front. Playing the long game while pursuing stories isn’t always easy. Or popular. In an era wherein every thought and opinion is blurted out unfiltered into the Twittersphere it may seem decidedly old school. I make no apologies for that. It isn’t something that comes naturally to the impulsive or impatient. But it can pay rich dividends to those wise enough and strong enough to play it and play it well.

And my colleague? OK, so he didn’t get to break the story first but he was rewarded with an exclusive in-depth interview a few days later with the key participants. His story was much more accurate and insightful than any of the earlier breaking reports which were decidedly short on details. As well he got an enhanced reputation for fairness and trustworthiness amongst his contacts, employers, peers and readers. And perhaps most importantly, he feels that he handled the story the right way, treating his sources with dignity and appropriate respect. I’d call that an outstanding example of playing the long game at its absolute finest.


Posted on August 30, 2013 at 9:00 am by editor · · Tagged with: , ,

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