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What I’ve Learned in the 17 years of Being my Own Boss

With escalating headlines on the gig economy, Uber’s definition of employment being parsed, politicians focusing on the economics of on-demand employment, and the entrepreneurial profiling of the upcoming Generation Z, I felt it was time for a post about what it means to be a designated 1099. The good, the bad and the fuzzy.

Two things to clarify before I get to the good stuff:

1) To be clear, along with tongue in cheek, I tell people that I have been a consultant for 17 years, of which I have taken 2 “real-job” sabbaticals (equaling a total of less than 2 years).

2) Personally, I eschew the term freelancer. While free does elicit a response it also sets up an expectation. The #1 thing I hear from those who are independent is they are often spending more of their time collecting payment than doing the work. That is wrong. Just sayin’.

To get at the singularity of being your own boss, I’ve created a list (like that hasn’t been done before) to peruse based on your interest and/or need in being a solopreneur. There are a lot of moving parts (I picked some that I feel are important and left some out because they are thorny); I hope I’ve covered the most pertinent ones here.

1. A checklist of skills for being a successful independent.

Here are the 4 traits that are imperative to being out on your own:

i) Organized
ii) Disciplined
iii) Passionate about what you do/offer (you’ll be talking about it all the time)
iv) The ability to get along with almost every personality type (you’ll work with them all)

I hope it is implied that you should also be comfortable being independent.

2. Treat your business as a business.

One of the reasons that 1099’ers “get no respect” is because often others see us as temporary, in-between full-time jobs. And the best way to counteract that is to act like your business is a business. Here are some examples:

– Separate your financials so that there is clear delineation between your professional and personal, specifically checking accounts and credit cards. (More about savings accounts in #7.)

– I pay myself a salary; it is clearly noted in a balance sheet of my business.

– Get in a habit of looking at the data of your business: conversion rate, best referrers, sales cycle, cost of doing business, allocation of time use, and year-over-year income (as a starter list).

3. A very important detail of acting like a business (a.k.a. Uber’s headache).

One sticky area that is not always detailed out is how important it is to not only have the appearance of being your own boss, but being sure you have more than one boss at a time. This is the contractor vs. consultant issue that is clouding up (okay I’ll take the pun on that one) the courts in California. Because I am not a lawyer and all states are different – let me just jump to how I manage this for my own business. I always have several clients within the year. More often than not I have them overlapping each other. There is a clear paperwork trail that establishes me as being an independent entity and not an employee of any of my clients (something my clients also want). Per the likely growth of the gig economy, this is going to have to be better defined, with clear guidelines, and with more consistency across the country (think rules for the Information Era vs. the Industrial Era).

4. To run a business you need marketing, sales, HR, accounting, legal, and tech support.

You need a lot of skills beyond what you are offering to the marketplace. Pick and choose which ones you really want to be and outsource what you need to. Get smart about legal (that could be a whole other post), but get a lawyer when you need one. I run my own P&L but I don’t mess around with taxes – I outsource to a professional accountant.

5. Uncle Sam isn’t so friendly and you have to deal with him more often.

At the federal (and in many cases the state) level government is still under the impression it is the 50’s when it comes to company structure. The biggest burr in my butt is as an independent I pay into Social Security twice, once as the employer and the other as an employee and … wait for it … I only get one of those back! (I’m totally simplifying this but the gist is you put in more than you get out.). Also you have to pay taxes quarterly not just once a year! Put in your calendar April 15th, June 15th, Sept 15th and Jan 15th as a reminder. Finally, when it comes to taxes – be prepared. The one thing I do is separate out 40% of every incoming check for taxes and costs of doing business (think: squirrel, nuts).

6. Here’s to your health.

Geez, independent or not, health care is an abyss. You need it and it is hard to get as a single payer (to be transparent, I am totally pro- everyone being single payer, and especially so if the ranks of 1099’s are getting bigger). This is definitely a big portion of the costs of doing business. There are options: Freelancers Union, I know some consultants using Obamacare, and there are new entrants like Oscar. This is truly a personal choice. The answer shouldn’t be “I’ll go without.”

7. Here’s to your financial health.

I’ll make this quick because it can easily take up its own post – instead of 401(k)’s, as a solopreneur, you have a great advantage being able to save through a SEP-IRA (Simplified Employee Pension), or as I like to call it Self-Employed Pot o’Gold. Read up about this, pick one that is right for you, and stuff it full of the allotted money every year. (Every major fund company has them, plus the banks. If you have a financial advisor, ask them. It is overwhelming but worth the several hours of learning and choosing … or just take a dart throw and start one.)

8. Make it legal.

Your business should have a legal definition. This is another area where there are no easy answers, but not looking for an answer that suits you is fraught with peril. Start by searching for legal definitions of a Limited Liability Corporation (LLC) and S/C-Corp. There are costs of doing business for both. Talking to a lawyer and an accountant should be part of your investigation. Bottom line this legal definition should separate your personal from your professional liabilities.

I’ve left out a lot because there is a limit to a person’s ability to list them and read them! Didn’t get into all the different insurances. A biggie I get asked all the time is how to market your business and convert business, which is missing here. Also left out the importance of tracking your time (big benefits when you do). Didn’t address some of the lifestyle issues of solopreneurism (e.g., feeling isolated, missing working with others, having freedom, time management). If you are interested in any of these – or have any questions – post them in a comment and I’ll do the best I can to answer/guide; might just write another post. (Disclaimer: I do run my own business and will likely have time delays in getting answers or post up quickly!)

I’ll wrap-up with two parameters that are often mentioned as being benchmarks of a successful independent:

1) If you can make it work, string it all together, for 2 years; mythology says you’ve made it. You may know sooner than that if you want to be doing it.

2) A wise mentor told me: you will know you’ve made it when you fire your first client. Which was heresy to me. But she was right. It means you know whom you can help and whom you can’t.

Learn more about Beth Temple at Linkedin (https://www.linkedin.com/in/btemple)

Is Gen X the “Jan Brady” of the Generations?

jan brady

Which one is your Jan?: Classic TV Jan…or more recent Movie Jan?

To Jan Brady, it always seemed like everyone else was getting all the attention. If it wasn’t little sister Cindy, then it was, of course, big sister “Marcia, Marcia, Marcia!”

Similar to this classic example of “middle child syndrome” from “The Brady Bunch,” it often seems to Gen Xers that they are caught in the middle these days. For, while everyone’s busy talking about Baby Boomers and/or Millennials, members of Generation X are left there, ignored and sandwiched in between, wondering, “Hey, What about us!?”

Having entered the workforce during tough economic times, many Gen Xers, unfortunately, missed the boat that Millennials are about to set sail on. Gen Xers showed up on time, wore a suit, didn’t ask for perks, waited years for that big promotion that never came, and did all the right things…only to now find Baby Boomers tripping over them to shake hands with the GenY/Millennials.

So what does a Gen Xer gotta do to get some attention around here? Like a middle child who sees his or her younger sibling reaping the benefits of being the “shiny new thing” — and with the Boomer generation still calling the shots (for now) – perhaps it’s time to give Generation X a little love.

But before we do, let’s recap where we stand as we wrap up our four-part series on generational issues in the workplace: In post #1 we explored the Five Things Millennials Need to Know When Being Interviewed by a Baby Boomer. In post #2 we discussed Five Myths About Millennials That Boomers and Gen Xers Need to Let Go Of. And then in post #3 we flipped the traditional hierarchy on its head to see what happens When the Tables Are Turned: 5 Things Boomers and Gen X Need to Think About When Being Interviewed By a Millennial.

So now, let’s dig in to post #4 as generational expert Brad Szollose and I discuss the Top Four Things that Gen Xers need to do to avoid being the Jan Brady of the office:

1. Take back your power

As their label suggests, when we Baby Boomers came along (born post-WWII between 1946-1964), there ended up being a LOT of us. In many cases, as we pointed out in previous posts, at work we were expected to just sit there, shut up, and take anything and everything our bosses threw at us…literally. Todd had a boss throw a box of pens at him; and I once had a boss throw a punch at me.

 So when Gen X (born between 1965-1979) entered the workforce, they, too, were expected to pay the same dues: work hard, keep their mouth shut, take the abuse, show up early, stay late, obey the rules…and maybe, some day, when the big bosses felt you’ve earned it, they’ll give you a title and a corner office.

But then suddenly, Gen X, after a decade of putting their heads down and doing what they were told, after riding out the recession and waiting patiently for the economic ship to right itself…along came the Millennials (born between 1980-2000) saying, “Excuse us, please…you had your chance…now it’s our turn.” Gen X, outnumbered and beaten down by one of the worst economies since the Great Depression, found themselves pushed aside and drowned out by the more demanding, more vocal, and more favored Millennials.

 Regardless of generation, every employee desires the basics: decent working conditions, fair treatment, fair compensation, etc…, but the Millennial generation (as discussed in our previous post) is the first to walk into companies saying, “If you are NOT going to pay me what my college diploma is worth, enough to pay off my student loans and to move out of my parents’ basement, then I want perks: a laptop and smartphone, flexible hours, free snacks and lunches, and paid time off to help make the world a better place.”

Boomers at first thought this was outrageous entitlement; after all it took them twenty years to earn any of those kinds of perks. But eventually they realized it was just smart business. Pay them less, but make ‘em happy in other ways. Or they’ll just walk out the door. And as this is going on, Gen X is sitting there with their mouths hanging open thinking, “Are you kidding me? I was lucky to even HAVE a job…and they’re asking for all these things…and getting them?”

But here’s the situation, Gen Xers: You may not realize this (especially those of you who have been so beaten down), but with the economy finally improving and with your having paid your dues, you’ve earned some serious clout – and your time has come. Being halfway between Boomers and Millennials, there’s a good chance that you possess many of the most valuable qualities of both. You have the work ethic and experience of a Boomer, combined with the flexibility and adaptability of a Millennial.

So step up to leadership, and take back your power. Sharpen your communication skills, and enhance your influencing skills. Seek out feedback and mentorship from those above you, and be willing to learn from those below you. As more and more Baby Boomers retire with each passing day, you want to position yourself for the next level and the next challenge. The days of “sitting and waiting to be called” are over. You’ve been waiting for your chance to seize the day…and that day has come.

2. Bridge the Generational Divide

As Todd and I are Baby Boomers writing from our own first-hand experiences and perspectives, we wanted to seek out the viewpoint of a Gen Xer so we reached out to Jeff Schwartzman, the head of Learning & Development for industry-leading financial services firm Liquidnet to get his thoughts on the subject. 

Jeff commented that while he often thought of himself as more of a Millennial than a Gen Xer, after interacting with a number of his organization’s Millennial interns, it quickly made him realize how far apart he was in so many ways. And yet, he also realized that there was so much he could learn from them. He emphasized that the main strength that Gen Xers bring to the table is that they are well-suited and well-positioned to bridge the generational divide as a result of possessing many of the best traits of each of the generations that came before and after:

“Gen Xers are incredibly important to the productivity of an organization. They have the years of real-world business experience that Millennials don’t have, and yet the openness and flexibility in their mindset to innovate and implement new ideas in ways that many Boomers may not. And as more and more Boomers retire or become farther removed from the latest trends and technologies, and while less-experienced Millennials are still getting their feet wet, the Gen Xers who have been patiently waiting their turn are now ready to stake their claim and step up to leadership.”

Building on Jeff’s thoughts, Generation X, having the very best strengths of BOTH generations, and with hiring picking up, will be more and more in demand as more and more Boomers retire, leaving a huge leadership gap. So with their unique understanding of both the old and the new, the past and the present, members of Gen X are well-positioned to carve out their own paths.

3. Pump up your ambition and step up to leadership

Several recent studies have found that many members of Generation X (and even more Millennials) do not want the pressure and responsibility of a leadership position. Is it fear? Is it a lack of ambition? Or is it a mindset of embracing comfortable stability and avoiding the target on the back that comes with a leadership role. Gen Xers, especially, who have lived through the trauma of seeing so many of their peers unceremoniously laid off and are still somewhat shell-shocked, often think and feel, “Why bother?”

But, as mentioned, there is a leadership void going on out there, and the gap is going to get even bigger as Boomers retire. And, because the size of their generational pool is smaller than the number of Boomers dropping out of the workforce, there will be less competition for those openings. 

So it’s time to use this situation to your advantage. Instead of shying away, be proactive, change your mindset, and step up to the challenge. Your Millennial coworkers are certainly not going to be shy about speaking up for what they want, so you shouldn’t be, either. As Jeff said previously, “stake your claim.” You’ve earned it.

Most traditional companies still see age and experience as two of the key factors in making management hiring decisions. If you are being interviewed for more senior roles, be open about how much you have learned, the experiences you’ve gained, the results you’ve produced, and how you are well-positioned to navigate and negotiate between the three generations. Prove to them that you can handle the Big Chair.

And if you have an opportunity to seek out any management training or leadership development, do it NOW. A Harvard study found that most companies do not put their people through any kind of leadership development until they are in the 40’s, while many of them have been in leadership positions since they were in their 30’s. This, basically, means that they’ve had ten years to operate without any training for this role…and to develop and reinforce all kinds of potentially bad habits! Don’t let this happen to you.

4. Move up…or move on

If you have paid your dues, worked your way up the corporate ladder, and are still being left behind for one promotion after another, perhaps it is time to take a page from the Millennial handbook and move on. Millennials proactively seek out work environments that respect their individual contributions and organizational cultures that treat them as equal partners in the success of the company –- regardless of age or title.

And while loyalty to a company is an admirable trait to have, we all know that company loyalty to employees has, in most cases, gone the way of the dinosaur. As Dan Pink put it in his book, “Free Agent Nation,” even when employed by an organization, we are all, essentially, free agents these days.

And while there used to be a stigma about leaving a job before you’ve been there two or three years, those days are gone. While you don’t want to be a “job-hopper,” you also need to look out for Number One. So if you have maxed out in your current role and all signs seem to be leading towards a dead end, there is no better time than now to make your move.

I was recently attending a Vistage event that was being held at a brand new law firm when Amy came running up to me to say hi. One of the top IP lawyers with one of the top law firms in the country, I couldn’t imagine what she was doing there, hosting the event. “I quit three months ago,” she blurted out, “and I couldn’t be happier!” 

Turns out she had been disgruntled at her old firm for years, but didn’t even realize it. After 17 years and millions of dollars generated, she was still being kept at bay for partnership. She just figured this was all part of the partnership promotion process: waiting and suffering. But something I had said over a year ago made her realize that something was missing in her high-powered career: appreciation and recognition.

So she left her prestigious, old-school law firm for a small, new firm that immediately put her on the fast track to partnership. She looked younger, happier, and was doing better than she could have ever imagined. And it wasn’t the money; it was a sense of appreciation for working her tail off that she had been needing.

 So just as Amy did, if this is how you are feeling and what you’ve been thinking, it may be time. Though it’s never easy, give yourself permission, be proactive, push yourself beyond your comfort zone — and the safety and security of the status quo — and explore the world of possibilities that exists out there. Not only will you be glad you did, but you’ll ask yourself, “What took me so long?”

In closing, as a Gen Xer you have struggled through some tough and turbulent times, and never got to share in the glory years of the Baby Boomers. But on the other hand, there is no time like the present, and with things finally picking up out there, it is finally your turn to shine.

This wraps up our four-part series on generational issues in the workplace; I hope you enjoyed it. My sincere thanks to Brad Szollose for contributing his expertise and his experience: Brad, you are, indeed, the master of your domain!

When the Tables are Turned: 5 Things Boomers and Gen Xers Need to Think About When Being Interviewed by a Millennial

millennial_boomer_interview.jpgIn our last post, we discussed Five Myths About Millennials That Boomers and Gen Xers Need to Let Go Of, and in our previous piece we explored Five Things Millennials Need to Know When Being Interviewed By a Baby Boomer.

Now in this, the third of our four-part series on generational issues in the workplace, we want to flip the traditional hierarchy on its head and discuss the increasingly common occurrence of how (and why) Baby Boomers and Gen Xers need to think, and act, a little bit differently when it is a Millennial who is in charge.

In the old days, positions in the organizational hierarchy were based mainly on seniority and experience, but as we all know, it’s a whole new world out there wherein age and years of experience no longer matter when it comes to who reports to whom.

Last year, I was quoted in this Forbes article entitled When A Millennial Is The Boss, but before Boomers and Gen Xers can even get to the point where you have a younger boss, you need to make it through the interviewing process. And you need to realize that a lot has changed since you first started out.

So with that goal in mind, here are five things that generational expert Brad Szollose and I agree that Boomers and Gen Xers need to think about when being interviewed by a Millennial:    Read More →

5 Myths About Millennials That Boomers and Gen Xers Need to Let Go

myths_millennialsAs part of our continuing series on generational issues in the workplace, my last post discussed Five Things Millennials Need to Know When Being Interviewed by a Baby Boomer.

Co-written with generational expert, Brad Szollose, today’s post explores and dispels some of the common – and counter-productive – myths that Baby Boomers and Generation Xers often have about Millennials.

Myth #1: Millennials are entitled, and have a bit of an attitude

One of the most common complaints Baby Boomer bosses have about Millennials is that they have a sense of entitlement, resulting in some part from a co-dependency with their “helicopter parents.” There are tons of (humorous, and even ludicrous) stories floating around online regarding Millennials bringing their parents along on job interviews, or having mom contact HR to negotiate a better benefits package. Boomers, can you imagine your parents coming to your office in your mid-twenties and making a scene like that?
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5 Things Millennials Need to Know When Being Interviewed by a Baby*

(*a response to Todd Cherches’ column; Five Things Millennials Need to Know When Being Interviewed By a Baby Boomer)

1. Babies can’t understand what you’re saying
You probably can’t understand their questions either. So it doesn’t matter what you say. The important thing is to smile. Every few seconds make a surprised look by opening your mouth wide and arching your eyebrows. Avoid blowing a raspberry on their belly; while fun, it constitutes harassment.
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Five Things Millennials Need to Know When Being Interviewed By a Baby Boomer

Millennials Baby BoomersOne of the hottest topics out there right now is the subject of generational differences in the workplace.

As discussed in my recent post entitled, “Spanning the Decades: Career Advice for Every Age and Every Stage,” four generations – Traditionalists, Baby Boomers, Gen X, and Millennials/GenY – currently work together…leading to a variety of commonly-recognized workplace issues and complications.

One of the most common and challenging examples of this is when these different generations cross paths in the job interviewing process. So I am often asked by my clients and my students for tips on how to navigate this treacherous terrain.

But rather than taking on this daunting challenge all by myself, I decided to turn to one of the most prominent experts in the field of generational differences in the workplace: my friend, Brad Szollose, the author of “Liquid Leadership: From Woodstock to Wikipedia – Multigenerational Management Ideas That Are Changing the Way We Run Things.”

This post will be the first in a series of co-authored articles on this topic of interviewing across generational lines.

One note to keep in mind before we start: We never want to stereotype people based on their age or generational affiliation (as there are always exceptions to every rule). But, from personal experience and much recent industry research, there are certain trends and patterns that we find out there — and, thus, advice we can offer – that might help you to more successfully bridge the generational divide. And, as this is just two Baby Boomers talking, if you have any additional thoughts on the subject, we’d love to hear insights from ALL generations, so please feel free to dive into the discussion by contributing to the comments section below. With that said, here we go…

   Read More →

Ice, Rice, or Mice? The Burden of Communication is On You – 6 Tips To Help You Communicate

miceglass.jpgMy Diet Coke had gotten warm, so I asked the waitress for “some more ice.” A few minutes later, instead of the ice, she brought me another bowl of white rice.

I said “more ice”; she heard “more rice.” So whose fault was it? (And good thing I didn’t say “some ice”…or I might have ended up with “some mice”!)

It happens all the time: We say something that is crystal clear in our own mind, and yet the person on the receiving end hears something completely different. The ice vs. rice mix-up was a relatively low-cost, low stakes mistake (and, I actually wanted some more white rice anyway), but what if the stakes were higher?    Read More →

Slow Down! Thinking Too Fast Could Ruin Your Job Interview

thinkerSo, you have a job interview or a big meeting coming up with the boss or an important client. You’ve done your homework and you’re prepared, primed, and pumped up. But have you thought about your thinking speed?

We all know that interviews and high-stakes meetings can be stressful, and when nerves flare up, our tendency is to think and talk too fast, leading to our blowing that meeting that we prepared so hard for.

In his now classic book “Thinking, Fast and Slow,” Daniel Kahneman takes a deep dive into how we think – and teaches us how we can think more effectively. According to Kahneman, one of the biggest problems is that we tend to think too fast.    Read More →

You’re Being Scouted! Five Tips To Make Sure You Are Poachable

It’s not your imagination, jobs are now hunting for you, not the other way around.

A newly released report from The Federal Reserve Bank of San Francisco says that, “Roughly three-quarters of job switchers did not report having looked for a new job,” and “workers who switched jobs seem to have been actively sought out and recruited by their new employers.”

This means that the bulk of new hiring isn’t coming from candidates applying to positions but rather companies scouting individuals through active recruiting and referring.

So what does this mean for you?    Read More →

15 Fascinating Books to Help You Become a Better Thinker in 2015

Books 2015 imageAmong the fastest-growing topics on business bookshelves these days are those that examine how we think, how we make decisions, why we make mistakes, how we learn, and how we lead.

These titles, which may be listed under the headings of social or behavioral psychology, behavioral economics, learning theory, or the increasingly popular title of “neuroleadership,” show us not only how we think, but also how we can start to think better.

Think about how many decisions you’ve already made today: What time to get up. Which toothpaste to use. What to wear. What to have for breakfast. How best to get to work. And what to do when you get there. From the minute we wake up, throughout the day, and until the second we fall asleep we are always thinking, whether we realize it or not.

But despite all that thinking, how often do we actually STOP to think about thinking? That’s what this year’s list is intended to help you do. Once you start thinking about HOW you think, it becomes pretty hard to stop. And with this heightened self-awareness, you will soon find yourself having greater insights, making better decisions, making fewer regrettable mistakes, and acting more efficiently, effectively, and confidently.    Read More →

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