This past weekend we made the trip to our new accountant to get things aligned for the past year and what lies ahead. He looked at all the 1099’s we had for the year and smiled a bit. “At least it looks like you don’t have to worry about a job cut with so many sources of income,” he said. True, but it served as a reminder for those who choose to go out on their own…you say you work for yourself, but the reality is you usually work for many.
I was reminded of those paths taken and people worked with when we got home and I decided to clean out a file cabinet with so many forms…NDA’S, proposals, business plans to review, old tax forms and time sheets…from over 18 years of working “for myself.” The shredder was quite busy as I went through so many reams of paper no longer needed, but it served a s a great reminder of the places we have been (and some we never did) the paths we have crossed, and the work done over what has become more than a second act (its like the ninth act) on ones own. There are so many businesses that have come and gone, leagues and properties (PHF, Drone Racing League, International Swimming League, Rugby 7’s, World Team Tennis, Bloomberg Sports, etc. etc.) that have come and gone, along with so many worthwhile projects, including films, plays and books, that had a finite start and end. A good amount of startups with great ideas that were sold off, or just didn’t have the capital to make it through, and a running list of amazing opportunities that reinvent themselves and come back as needed. Heck there were even some things that made it into the shredder that I had long forgotten about, interesting ideas and stories and people that have drifted off into other areas, many of which you see or hear about time and again in a business of people and places much more than things.

More and more people, especially those 40 and up, have either entered, or have been thrust into, the employment search pool, many times not by choice. And although the phones and emails for people looking for advice and to network for a job or a career change never seems to subside, the spring seems to bring on new angst and yet more faces each year. Many call because I have been in that pool, the work for oneself pool, and luckily, it has worked out OK. As I tell people, it wasn’t by choice, and the path really chooses you sometimes more than you choose it, but it is the path I have been able to navigate, and I am always more than willing to try and share what I can through the experiences I have had, but also because of so many that I have spoken to or spent time with over the years who have either figured it out or found another road to travel. It’s quite the fluid world we live in.

So it is with March Madness now here that I re-read a piece in the New Yorker about the anxiety caused by freelancing, and for that matter, the consulting or entrepreneurial world that many either choose or get thrust into, many times for reasons beyond their control. The piece had a host of points about the darker side of being on one’s own; the “always on” for working with whomever needs you at a given time; the angst over steady, or not steady income; the questions of real vs. perceived freedom, and the loneliness of being on one’s own, usually without a net.
All of that, for the most part, can be true from time to time, and for a country where a Wall Street Journal report recently said that over sixty percent of the workforce can be thought of as “consulting” in the next decade, the scariness can certainly be daunting. The country is aging, many big businesses are looking to reduce headcount, insurance is always an issue when balanced against cost, and quality of life is and should always be, a big part of being able to grow up, and old, with some grace and dignity.
However dark the story was, there were also the positives that were pointed out; choosing work life balance, the ability with technology to be anywhere and doing anything for select positions; the ability to continue to learn and evolve as a person, and for some fields, the ability to master and specialize to an audience which needs certain areas of focused expertise.

There was also one piece, well a few pieces, that the story left out that are really important for those either on, or considering going out and trying it on one’s own, or with a smaller select group of colleagues who may share space and ideas but have complimentary skill sets. When you say you “work for yourself,” as I have seen and done it, you actually are working for everyone else. Unless you are a carpenter building tables, or an author storytelling in whatever medium you are in, the world of consulting and freelancing means you are working with many, many people all with various and sundry needs. If all goes well, you also get to work on great projects and with smart people of your choosing. However sometimes you try and take the gig with the impossible as an end game. Those are things at this stage I try and avoid, and when talking to people in the pool, I always try and caution for the reality check vs. the cashing of the check. Your sanity, and your reputation, are really key.

So are there challenges and angst in the consulting world? Sure. But they are really not different than most people in any position where they strive to do well and where strong results are expected, especially in a very fast paced world of sports and entertainment media. There can be high risk, but there is always high reward. The biggest difference after being in the consulting or freelancing pool? If you do it well, and if your body of work can speak positively, your control over the ‘who” you work with becomes a bigger variable. Rare is the time when working in one fixed place where you have control to say no or to move on from a person, or a project, that you either may not be able to succeed with or don’t want to work with.
That DOES NOT mean you can’t and shouldn’t be challenged, and being on one’s own means always looking to find new areas to learn or to challenge yourself or reinvent yourself. It’s not for everyone, and I have said I did not think it was for me for quite a while, but the lessons learned, the challenges address, and most importantly the people and experiences you come across can out distance the angst for the long term.
So for those on their own, buy your accountant a beer or a glass of wine or a piece of cake after he or she pulls all your threads together in the coming weeks. It may look a little messy and complex, but when you stand back, with positives outweighing challenges, it may just paint a nice little picture you didn’t see at first. And if it does, pass the positives on.
Trust me, there are more jumping or being pushed in every day, and they sure can use the lift. And while the shredder gave me more space in the file drawer, the memories that came up of people and places and projects past continue to fill a lifetime of work and the exercise served as a great reminder of the “why” you do what you do, either on your own with others or in a collective. The paper may be repurposed, but the experiences and opportunities are never lost.


The Joyful Reminders of Sport Abound This Week…