How to Handle Gaps in Your Employment

Seek it, claim it, and own it – Issue #54

The short vacations we have in the U.S. are pretty pathetic, and most people don’t even take those. You barely have time to decompress, unwind, and relax before it is all over, and you’re back in the office again.

Months off are what you need to reconnect with yourself and your loved ones and think about what you really want out of your career and life. But when will you ever get that chance?

Taking a break between jobs is a rare opportunity to claim that time. You can intentionally delay your job search to take an extended vacation before diving back into the working world. Or, if you’ve already landed a job offer, you can delay your start date.

You’re totally free of the demands of your old job, and none of the work for your new job has started yet. There’s only one problem. Most new employers want you to start work right away. They may tolerate a short break — if you’re lucky.


My first experience seeking a gap

I remember wanting to take a vacation between jobs several years ago. I had been through an intense, stressful period of work without time off for years. So, I wanted to take a breather, spend some time with my family, and decompress before starting my new job.

While I actually needed more time, I knew that two weeks was probably the most I could take due to the urgency of the new job’s demands, which seems silly now.

Side note: One benefit of aging and perspective is that you see how ridiculous a company’s definitions are of “urgent” and “important.” In the big scheme of life, none of that matters.

But, my new boss didn’t even want me to take those two weeks off. He kept pressuring me to start right away, the Monday right after I left my last job on Friday. He said they couldn’t wait two weeks for me.

Luckily, I stuck to my guns and took the vacation anyway. Did the world end at the company because I started two weeks later? Of course not.

Did I get the rest and relaxation I needed so desperately? Did I truly clear my head between jobs? Of course not. A short vacation like this just isn’t enough time for that.


Finally embracing the gap

I took a “gap summer” after Yahoo to reconnect with my family and think about what I wanted to do next. Plus, I was excited about the possibility of having a real summer vacation for the first time in over 20 years.

I often tell people that it takes a few months to clear your head from a past company, especially if you worked there for years. You’ve been so immersed in that culture, and way of thinking, that you can’t even envision creative alternatives for your next job.

My immediate thoughts were to find a job that was more of the same — another exec role as the Head of Product and Design for a Tech company. I interviewed for a couple of positions, but nothing felt right.

As the weeks and months went by, I kept asking myself “Why” and “What if…” questions. I thought about all of the things that I enjoyed about my past jobs. I also listed all of the things that I disliked about those jobs.

What if there was a way to do more of what I loved about the work, without all of the crap that made those jobs suck? Maybe I no longer wanted a traditional job at all? Crazy talk, I know. But, the time to free my mind, question everything, and think creatively lead me down a very different path to today.

Yes, my most recent gap year may have been a little extreme. But, I think that a mini version of the gap can be enjoyed by anyone and provide you with numerous benefits.


You can truly rest and recover

The first week is full of thoughts of work. You wake up in a panic thinking you’re late for your commute, but then remember that you’re on a break. Do you remember that first morning of summer vacation when you were a child? Yeah, it feels like that.

The second week is plagued with vague stress that things are piling up, your boss is upset, coworkers are scheming, etc. But, by the third week, you can finally relax and enjoy yourself. You know that you have to return to work, but it can wait. Things will be ok.

It is a rare experience to have as an adult. How often have you had a significant amount of time when you were in total control of how you spent your days? You don’t have to go anywhere you don’t want to go. You don’t have to do anything that you don’t want to do. You don’t need to see anyone that you don’t want to see.

The feeling of relaxation is amazing. But, you can’t stay in this mode forever. At some point, you’ll want to start thinking about ways to use your time more constructively. It is a rare opportunity, so you should make the most of it.


You can invest in yourself

Use this longer period of time to invest in something you’ve always wanted to do for yourself. Create a regular fitness routine. Take interesting classes. Start journaling. Experiment with meditation. Read some books.

Everything you do will enrich the story you will tell later (more on this at the end of the article). All of this is an investment in yourself, and that always has a positive ROI.

If there are skills, experiences, and knowledge that you want to acquire to improve your value in the job market, now is the time to do it. If you want to explore ideas for starting up your own business, you don’t need anyone’s permission.

The best investment you can make is in yourself” — Warren Buffett

Create some goals and make plans for utilizing your time. You already took a real vacation at the beginning of your break, right? Now you can get to work. But, this time you are working for yourself, instead of someone else.

Take the time to really understand who you are now. We are not carved from stone at birth and set in motion. We grow and change and evolve during our entire lifetime. Who you were when you took that last job may not be who you are today.

Ask yourself what it is that you really want for your career, and for your life. What do you want more than anything else?


You can ask yourself tough questions

After you make it through a couple of months of this newfound freedom, you’ll start to ask yourself “Why” questions. Once you’ve finally cleared your head from the cobwebs of work, you can start thinking about things that matter to you (instead of pondering how to squeeze more efficiency out of your daily standup meetings).

  • Why do I want that next job?

  • Why do I have to go back to doing what I’ve always done?

  • Is this career path really want I want to do for the rest of my life?

  • Is this all there is to life?

  • What if I didn’t go back?

  • What if I stayed here and opened a banana stand on the beach (There’s always money in the banana stand)?

I can’t promise that all of your thoughts will be rational. My ideas certainly were not. You wouldn’t believe some of my crazy business concepts that I dreamed up.

What matters is that this time has cleared your head of the old so that you can be truly creative while thinking about the new. You may still decide that your old career path actually is right for you. If so, you can recommit to that plan with renewed passion and vigor. This gap time and recommitment will only energize you more since you know that it truly is what you want

Or, you may realize that you need a change.


You can reconnect with friends and family

If you’re a driven and ambitious person focused on rapid career growth, it’s not uncommon that you’ve spent less time with friends and family than you would like. I know that it was true for me.

After I had been home for a few months, my young daughter said that she was so glad that I was finally spending time with them. She told my wife that she had always been a little nervous around me because she didn’t really know me. I was a stranger in my own home.

That broke my heart. But, I only had myself to blame. I had been working nights and weekends for almost a decade to focus on my career. I wanted to get promoted, move up fast, and make as much money as possible. In that pursuit, I almost lost what mattered most to me. A great relationship with my family.

Ultimately, I decided that the sacrifice wasn’t worth it, so I didn’t go back to a corporate exec job. I reshaped my career to get a high degree of freedom back so that I could really spend time with my children.

Of course, most people will return to their corporate jobs and that may be very necessary and right for you. But, reconnecting with friends and family may remind you of how important that truly is. It will empower you to adjust your work commitments to bring your life back into a better balance. Claim what you need. You deserve that.


However, manage your burn rate

If you’re not familiar with the phrase “burn rate,” it refers to the rate at which you are spending money in excess of your income. It’s usually applied to companies, especially startups. But, it can also be applied to your gap since you may not be generating any income.

The duration of your gap period may be determined by your savings. If you don’t have a big cushion, you may have to return to work fairly soon. But, you can reduce your burn rate by tightly managing your expenses. You can also engage in some revenue-generating activities.

In my case, I had saved up a decent financial cushion, and we aren’t that extravagant with our expenditures. I also started doing some part-time consulting work to extend my runway. My success with this was one of the reasons that I never did go back to a corporate job.

If you’ve been clever enough to establish passive income activities (e.g., rental properties, ad revenue, or other investments), you may be able to sustain yourself for quite some time. The general idea is that you are buying your own time back. It’s an investment in yourself to have the dedicated time that you need to figure out what you really want to do next with your life.


But, but, but…

I hear you. The dreaded “gap in your resumé.” Is that still a thing? I know that it used to be a huge issue with employers in the past.

“Oh, I see here that you were out of work for three months. What happened there?”

But, I think we’re moving beyond that stage of always being expected to be residing within the warm embrace of our parental employer. It’s more than ok to be on your own, decide how you want to spend your time, explore options, and invest in yourself.

Hell, I see that as a badge of honor you should proudly wear, not something that you’re nervous about explaining. Take control of your gap story.

First, have a story to tell

  • It’s hard to tell a compelling story if you haven’t made use of this precious time. If you’re already in the middle of a gap, tomorrow is a new day and an opportunity to rewrite your story.

  • As mentioned above, set some goals, make a plan, and start acquiring accomplishments. Is there some new skill or knowledge you’ve always wanted to learn? Now is the time. If you have an internet connection, it’s never been easier to educate yourself. If you don’t, get thee to your public library.

  • Leverage your talent, skills, experience, and network to start doing some consulting or advisory work. Paid gigs would be great (I did this)! But, unpaid advisory work is a better story than sitting on your couch watching Friends reruns. I’ve advised a number of startups and received nothing in return, other than meeting great people, expanding my network, and always learning something new.

  • Offer your amazing skills, experience, and knowledge as a mentor. Many high schools, colleges, and universities have programs that could use someone who has valuable real-world experience. One of my clients is doing this and loves it.

  • Volunteer your time and talent to a worthy institution or cause. Not sure where to begin? Charity Navigator provides a list of “exceptional charities that execute their missions in a fiscally responsible way while adhering to good governance and other best practices that minimize the chance of unethical activities.” It doesn’t have to always be about donating money. Share your time and talent, and you’ll learn something new along the way as well.

Second, own your story!

  • I don’t care how your gap came about. Even if you got fired and have been struggling to find your next job, today is the day you reclaim your story. Flip this around and own it. You are using this gap to grow and become more.

  • Be confident when you talk about your gap. No matter how it happened, you’re in the driver’s seat now. You took control of how that valuable time was spent.

  • Be honest about how nice it was to actually have some real time off. Who wouldn’t want a longer vacation, break from work, and time to spend with friends and family? Admit it and smile, because the person across the interviewing table is secretly wishing that he or she could take so much time off from work.

  • Be proud of how you value yourself enough to make an investment in your future. A few people never do. Some people rarely take the time. Most of us do it in the margins of our lives. Dedicating significant time to learning, growing, and improving is a rare thing indeed.

Third, let them know how special they are

  • Now that you own your gap story, and have shown how you’ve leveraged your precious time, it should become clear that it would take something quite special to make you leave your gap.

  • You’ve spent this time gaining a deeper understanding of who you are and what you really want next in your career (and life). Create a clear profile of the job and employer that maps to this new vision.

  • If you’re interviewing with a prospective employer, you can let them know that you have taken this time to explore opportunities and make the best choice for your next career move, not just any old job. You didn’t rush into something, and now you are intrigued by their opportunity.

  • If you already had a job lined up, and this gap period was used to recharge yourself and refresh your perspective on your life and career, you can enter your new job full of hope and energy. Your motivation and performance will be above and beyond anything you would have been capable of before if you had simply jumped straight from your old job to your new job.


Let me know

Have you taken a gap between jobs in the past and how did that work out for you?

If you’re intrigued enough to try it before your next job, I’d love to hear what you have in mind.

Check back with me and let me know how it is going!


Quick Tip

When you leave your job — either involuntarily or under your own steam — and you discover that you may be out of work for a month or more, immediately spin up a consulting practice. I know that this may sound impulsive and crazy, but hear me out.

Creating a consulting business and using it to update your LinkedIn profile eliminates that “dreaded gap in employment” that I mentioned earlier. You are no longer unemployed for months between jobs. You were doing some advisory work and consulting.

Note: You don’t have to actually engage in finding clients and landing paid consulting gigs if you don’t want to, but I do think it’s a good idea for a number of reasons. It helps replenish your financial cushion and buys you more time to search for a great job. It’s also a great way to network with people and stay active in your industry. Finally, you will find that almost every consulting gig turns into an opportunity to join as a full-time employee.

You don’t have to share who your clients are when you are interviewing and people ask you about your consulting business. It is quite common to have clients who are in stealth mode and don’t want their business to be revealed to others. You can simply smile and say, “Sorry, my clients are in stealth mode right now. I’ve signed an NDA and a restrictive consulting agreement. I can’t talk about what I’m doing for them.


Remote Jobs

  • Head of Design at Zapier. They’re looking for a Sr. Design Director to manage and scale their design organization. Are you excited to scale a user-centered UX design culture in a 100% remote company? You’ve managed or scaled design organizations at least on the order of 15 to 30 people. Specifically, you’re able to effectively manage design work through at least one layer of management. And have the experience to suggest how to structure a growing design team.
    You’ve scaled a product across the chasm and have seen both sides of it.

  • Director of Engineering at Blackthorn. They’re building something that’s not easy, they need the best, you can work from home, they have an annual company trip, and you’ll get a deep level of satisfaction. Director role, you’ll act as a hybrid scrum master, director of engineering, and overall efficiency-of-dev-process manager. They need someone who hits the ground running, not someone that needs training. Report to CTO and CPO.

  • Radiology Daily Support Analyst at MMY Consulting. MMY Consulting is committed to delivering the highest quality business and IT solutions to its clients. Their mission is to provide comprehensive consultation to public and private sector organizations seeking a true partner in their technology pursuits.
    They are currently seeking a Radiology Daily Support Analyst to join the MMY team. This is a remote 3 – 6 month project.

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