It is getting to be tax time in the U.S. As April 15 approaches, the whining and hand wrenching for those who may have paid enough, or not too much, or aren’t sure, gets to be more and more. Almost like the visit for root canal, tax time can bring on that feeling of dread.
Always around this time of year it seems like 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, for over 11 and a half years now, 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 Tax Time on the horizon for us that I read a piece over the weekend 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 present 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.
The other thing I am always reminded at this time of year on the “working for oneself” idea are those 1099’s that come in as the calendar turns. If it’s a good year, and you know how to manage your time, they provide a great little reminder of success and impact, but they also serve as a reminder that your work, especially if you work on projects big and small that have a fixed beginning and an end, can touch dozens, and yes dozens, of companies and people from all walks of life throughout a 12 month span. Many of those people I cross paths with on the freelancing side; media types, sales consultants, designers, copywriters, communications folks, actors among them; all point to having a good accountant to keep the balance and make sense of the piles of receipts, and those 1099’s, that become the mosaic of your financial life. It is quite a puzzle, but compiled well, the pieces can fit together into a nice narrative. 
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 for over a decade? 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.
