Tagged: career path

How to Level Up

I regularly hear from and read about technologists in a career rut. Unless one is both lucky and adept at predicting the future, experiencing some temporary stall can happen to professionals at any career stage. It may be the feeling of being stuck in an unchallenging role, feeling burdened by an undesirable skill set, or trapped in a company that seems difficult to escape.

Career stagnation in technology could be defined as a prolonged period characterized by limited project variety, no advancement or even lateral movement, few tangible accomplishments, and little exposure to any emerging trends. Some managers are aware that workers in these situations generally leave, so the managers may proactively try to satisfy staff by shuffling teams and providing more interesting tasks. Many managers have to focus on deliverables and may give little thought to the career development of their charges, perhaps throwing money at retention problems instead of providing challenges.

levelup copy

To “level up” could mean a promotion into management or technical leadership, a new start at a firm with increased opportunity, a role with autonomy and decision-making responsibility, or the ability to make significant improvements to skills and marketability. People that think about the leveling up concept often know what they want (or sometimes what they don’t want), but don’t necessarily see the best paths to get there.

Leverage the skills you have to get the skills you want

Most professionals view their current skills as a means to getting new jobs, but it’s useful to also think about skills as the key to acquiring other new skills. This tactic is most relevant when a skill set is dated and a previously strong marketability level is now questionable. Some will attempt to make a clean and immediate break from their old technologies or responsibilities into the new, usually with mixed results.

As an example, many COBOL programmers tried to enter the stronger Java job market following Y2K. Some applied to jobs with no Java experience hoping their COBOL years would be deemed transferrable, while others pursued certifications and self-study to ideally be viewed as a somewhat “experienced” hire. One overlooked strategy was to approach companies that were using both COBOL and Java in some capacity, with the understanding that the candidate was willing to write COBOL if provided the ability to also work with Java.

Most job seeking technologists have at least one ability that will help them contribute immediately to any other team or organization. It could be an obscure technical skill, leadership experience, or domain knowledge. Even if the skill is not something the person wants to use forever, it could be a key component to getting hired. Try to identify companies that may be looking for some specific expertise you can provide, even if it isn’t the most attractive tool in your bag, and be transparent about your willingness to do that less desirable work in exchange for exposure to skills that are in demand.


For those in the most stagnant of technical environments, taking on independent projects or open source may be the best way to gain experience and increase marketability. It’s usually preferable to learn new things on the job (because money), but being proactive about your career and keeping abreast of current marketable technologies will also show initiative to potential employers. The level up from personal projects almost always comes from an employment change.

Sometimes to level up you need to take a step back – or sideways

Careers aren’t always linear, and the expectation that trajectory needs to follow a strict continuous and incremental level of responsibilities is perhaps naive and potentially dangerous. Job seekers are often prone to placing too much weight on a position’s salary or (gasp) title without fully considering the position’s potential opportunity as it relates to future marketability and career development. Somewhat frequent movement between jobs is accepted in our industry, so positions can be viewed as stepping stones to future opportunities.

When evaluating new roles, whether with a current employer or another firm, imagine what a three or four year tenure in that role at that company will look like on future résumés. Will the skills likely to be acquired or improved in that role be marketable and transferrable to other firms? Accepting positions that come with lateral responsibility and compensation is usually a wise long-term decision when provided a more favorable learning and growth environment.

Rethink Career Path

The baby boomer generation probably helped define the image of career path and trajectory for many Gen X and Millennials that followed.  It was incredibly common for the baby boomer to remain with one company for their entire career, possibly move up the proverbial corporate ladder, and retire with a pension.  The typical baby boomer’s lifespan may have looked like

college/military → entry-level → low level management → higher level management → retirement with pension

For engineers, the problems of traditional career paths may be compounded.  To ‘move up’ and maximize earnings often means getting further from what you do best or enjoy (code) and the result may be to leave jobs more often than you should.  Management responsibility is not always on the engineer’s wish list, yet that direction may be the best way to earn more. There is a career point where salaries plateau, and switching employers becomes unsustainable as a method of increasing earnings.

Considering that statistics show the younger generations  are typically switching employers every three years, two things are clear:

  1. Employer loyalty is dead, and has been replaced by either loyalty to one’s own career (hopefully this is the case) or just the need for new challenges (boredom).
  2. We need to start looking at alternative employment and earning models, career path, and trajectory in a different way.

Entry-level and junior candidates in the tech industry often ask how long they should stay at any given job, how to get into management roles, or what options they have in their career given a certain set of skills.  I’m always amused when entry-level developer candidates inquire about getting into management, as if they are trying to get out of coding before they’ve written one line.  It seems that most are focusing their questions based around traditional baby boomer type standards of career path and earning, while very few are even considering what alternatives may exist.  “Layoff victim?  Go find another job, of course!”  “Not making enough money?  Get promoted or find someone to pay you more!

Aren’t there some other possibilities that one might at least consider?  In technology, the range of opportunities for earning are substantial and alternatives to the standard employer/employee mindset are somewhat vast.

As opposed to approaching your career as simply the search for new jobs, think about career for just a minute as a collection of ways to earn money while building your skills and marketability.  One of those ways is obviously to take a full-time job slinging code for the bank or insurance company.  That works for many people.

But what if your job isn’t paying you enough?  Naturally, you either try to get a promotion (which for engineers is often into a role that may make you less happy) or you go out and get a new employer.  Did it ever cross your mind, even for a second, to get a second job?  This second job could take on several shapes, so perhaps we should call it a second source of revenue so we don’t lead people to believe this will require 80 hours a week.

Or what if your job is not fulfilling professionally?  Do you ever hear about actors who will take peanuts to do the indie films they want and make up for it by doing a few summer blockbuster movies for millions?  This isn’t a perfect analogy, but it’s a valuable mindset.  I know independent contractors who may have three or four clients at one time, with varying hourly levels of commitment to each, different rates, and a range of project technologies.  It’s not easy to do, but it can be done.

If your day job is technically unfulfilling or not providing the necessary financial rewards, at least consider some of these possible options before taking the usual steps (listed by perceived level of difficulty, starting with least difficult).

Day job + moonlighting (contract) –  Could you make a few extra bucks and perhaps learn a new skill through a paid side project ?  If you have contacts that own businesses, they may be a good source for this type of work.  This could cure both your boredom at the day job and being underpaid.

Contracting – It seems the decision to go into contracting is often not made consciously, but rather based around a specific opportunity that leads to a contract and then an acquired appreciation for the lifestyle and money.  A proactive approach to entering contracting as a full-time endeavor is probably more effective, as you need to think like a business owner.

Contracting, multiple concurrent clients – This usually requires having a widely respected set of technical skills (a ‘name’), a network, and some basic business knowledge (not to mention time management and negotiating knowledge).  Not easy, but something to strive for and aspire to be.  Doing 50 hours of remote work a week on three different projects and getting paid for every single hour is probably fairly enticing for most.

Day job (full-time or contracting) + product – Could you supplement your primary income by creating some sort of product for sale?  Your product could be mobile apps, a web app with a subscription model, or even a tech book.  This could be time intensive at first and obviously requires some creativity for ideas, but also financially rewarding.

These alternative arrangements are not for everyone, and they may come with some associated risk.  The world of employment, especially tech pros, has changed significantly over the past two decades.  It’s time to start thinking differently about career paths and traditional employer/employee models.  Whether or not these options are right for you, they are worthy of consideration.

Job Tips For GEEKS: The Job Search is out and available in most ebook formats.  See the book page for more info on where to buy.