Dear Dana Workplace Advice: Career Planning in the Age of Digital Disruption

Welcome to “Dear Dana”, our regular column to give you career and workplace advice/coaching. Please write in and tell me about a career challenge or frustration you’re facing at the office! Today’s topic is career planning! – Dana Theus

Dear Dana: You wrote a post about how white collar workers are losing jobs to AI-enhanced software. I’ve heard alot about factory jobs going away to robots but not jobs on Wall Street. I’m a systems tester for a small custom software firm but I wear a lot of hats, including documentation and web programming. Since I read your post I’ve started reading more about how testing is being automated with higher-end systems. My boss seems totally oblivious. I showed him a couple of articles and he shrugged and said he’s seen it before and I should just keep my head down and do my job (in so many words.) I’ve been thinking of leaving this company anyway and now I definitely don’t feel like they are going to be at the leading edge of the changes happening in my industry. There aren’t a lot of tech jobs in my area though and I don’t really want to move. Got any advice? — Stuck (way) outside of Sacramento 

Dear Stuck,

Thanks for writing in with your inquiry. I don’t think you’re alone in sensing big changes coming that might overwhelm your company, and you with it. I’ve watched this space for a while and I’m truly amazed at the speed at which tech changes are starting to ripple through all industry sectors, including tech itself!

It sounds to me like you have three distinct issues you’re grappling with:

1. Deciding to stay with your current employer
2. Deciding to focus on systems testing or stay a generalist in IT/software development
3. Deciding to optimize for your geography or your career

Let me address each of these issues individually, as I think they raise different questions worth considering.

1.   Should you stay with your current employer?

Traditionally, employees assume their employers know what they’re doing and will be around for a while. We tend to focus a lot on how we’re treated to decide whether we want to leave or not. And we should pay attention to whether our employer values us! But this isn’t the only reason to stay or leave a company.

Disruption (digital and otherwise) is not only becoming common, it seems to be speeding up. The time frames between major economic disruptions is collapsing. Think of the time spans businesses have had in which to adjust between the following revolutions: agricultural, industrial, internet, mobile, genetic, artificial intelligence. The last four on that list have occurred in fewer than two decades, in my children’s lifetime.

As you can see from the chart below, businesses regularly go bust and are definitely affected by economic and global trends. Even if a company doesn’t go out of business, every organization is subject to dramatic change without much warning to the employees and even a lot of the managers. Many employees find this hard to believe, but company owners and boards tend to hold these kinds of difficult decisions very close, in part to keep anxiety at a minimum until they can decide what to do, until it’s too late for employees to prepare and the resultant decisions too-often blindside us.

I once worked as a Vice President for a startup that got a ton of funding. Then one day the executives were called into the conference room by our CEO and told that our funding was in the form of stock options, which had just tanked, thanks to the 9/11 bombings and we had to let 40% of our workforce go in the next nine days. To say that we were shocked would be an understatement, and it was the beginning of a very dark time for the company, which stayed afloat, but only by trimming even more in the ensuing years and changing its business model completely (I was long gone). I have a client now that’s at the top of its industry and really forward thinking. They just merged with another industry leader in their space and had a big lay off. They’re now starting to hire again as they see how the organizations are merging. I even have a client who was blindsided by a layoff from a government job she thought was for life.

You should always be preparing yourself for the job you want to have 2-3 years from now. <– Click To Tweet

In other words, you just never know how secure your employment is and you can’t assume your company will take care of you in a volatile market. It’s best to always be prepared for your next move to some extent. Given that the average job tenure is under five years anyway, this means that you should always be preparing for the job you expect to have 2-3 years from now.

My advice to you is to start reading up on the industry your company operates in to stay aware of trends. How will digital disruption affect your company or your customers? Is the industry growing or shrinking? How conversant in these trends are your managers? The owner? Do they seem to have plans to address them? If you seem more on top of things than your managers, that’s a bad sign. You can also ask more about the company’s financial health. Is it growing consistently? Are the contracts long-term? Are salaries regularly increasing? Are they making investments that will grow the company? If the answers to these questions are all “yes” then that’s a good sign, but if they’re all “no,” dig deeper.

The final line of questioning to pursue with respect to your employer is whether you can see yourself being happy in a job there for the next few years. Even if you don’t feel like you have to start a job search right now, it’s a good idea to explore your own work-life vision and regularly engage in career planning so you know what you need your job to be adding to your life in the years ahead. Every job comes with some headaches, but as soon as it fails to give you the things most important to you — experience, fun, good co-workers, interesting problems to solve, financial security, feelings of accomplishment — it’s time to consider your next move. This is a very personal decision, and too many of us wait until something goes horribly wrong to plan our next steps. Don’t wait! Learn to read the signs that it’s time to go early so you can make a smooth transition on your own terms. Your boss’ disinterest in AI might be one of those early signs. Dig deeper and see if you can find more — or not!

2. Should you specialize?

You say you wear a lot of hats, and in small companies this is pretty typical, and not necessarily a bad thing. I have had many generalist jobs that I enjoyed because no two days were ever the same. However, it’s pretty tough to turn a generalist job into a long-term career strategy if your goals include increasing income or higher levels of leadership. For these things, it’s a good idea to spend a chunk of your career specializing in an area that you enjoy and has the potential to grow in importance in the job market. Once you excel in such a specialty and begin to rise to higher levels of leadership you can begin to generalize more in a management and leadership capacity. You didn’t mention your age, but this can be a factor for many people, too. It’s common to be a generalist in your 20’s and again in your mid 40’s and onwards, but many people find that their 30’s is a great time to get to know a particular field very well.

Career misery is harder to climb out of than career boredom. <– Click To Tweet

While it’s good to research which job categories have the most growth and opportunity in the future, I wouldn’t stop there. Too many people choose a job category because it looks good on paper, but if it doesn’t feel good to you, don’t do it. If you’re going to specialize, you need to enjoy it or you’ll burn out and hit career crisis that can threaten other things in your life. Making a career change is very possible – and becoming more common – but it’s not easy especially if you’re miserable when you do it. Misery is harder to climb out of than boredom. The bottom line is that working is hard work so you want to do something that keeps you engaged and interested. Of the hats you wear, which one interests you the most long-term when you think about specializing in it?

As for your area of systems and software testing, I would think that career field will continue to be mission-critical for a lot of tech firms, but as with many job categories, the work itself may change. As automation and artificial-intelligence become more prominent aspects of technology platforms many programmers and systems developers will have to migrate just as the factory workers did to become “bot technicians” and team leaders who can manage teams made up of both humans and technology systems. It’s pointless to try to out-tech the machines so those who survive and thrive will become experts at changing and adapting to an increasingly automated workplace.

Should #leaders manage differently when they have bots on their team? <– Click To Tweet

When a bot can produce a team’s dashboard and highlight areas for focus before the team meeting more effectively than any of the team’s humans, the bot will effectively become a team member. More and more, managers and leaders in every industry and job category will need to manage teams made up of humans and machines and guide them through rapid change. The ones who are proficient in change leadership and human dynamics will excel because they keep the humans focused and efficient alongside machines that don’t get distracted by office politics and interpersonal conflict. So even as you brush up on your tech skills to learn to play with bots, don’t forget to invest in your soft skills too!

3. Should you optimize for your geography or your career?

You mention that you don’t want to move but find your area isn’t a tech hotbed. I don’t really have any specific advice for you here except to recommend you research jobs nearby, far away and in cyberspace (virtual) equally so you have a good understanding of your options. It’s always an eye-opener to discover options you didn’t realize existed (nearby or elsewhere) and it’s much easier to make a hard decision when you’re looking at information instead of when you’re relying on untested assumptions. I also recommend doing this research comprehensively, meaning that you should research your interests and options along many dimensions, geography being only one. There’s also your career interests, work-life-family needs, lifestyle and financial requirements, your personal strengths and growth desires and what companies in different industries and geographies have to offer you.

Be sure to include close family members in the discussion appropriately. I had one client who was surprised to find that his wife actually wanted to relocate when he’s been assuming she didn’t. The conversation about his job opportunities opened up a whole new line of discussion for their marriage and prompted her to consider a career change, too. Of course, you need to balance your needs against the needs of others, and that’s a very personal decision but it’s much easier if you’ve discussed the issues with those others first.

If you’re considering quitting a full time job to work virtually on contract, be sure to research the pros and cons of this. When you go contract, you’re taking on a different kind of risk, and different costs, than when you’re employed and you need to plan appropriately. I recommend that you moonlight a bit in the gig world before you quit to go full time.

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