Welcome to episode 169 of the Nerd Journey Podcast [@NerdJourney]! We’re John White (@vJourneyman) and Nick Korte (@NetworkNerd_), two Pre-Sales Technical Engineers who are hoping to bring you the IT career advice that we wish we’d been given earlier in our careers. In today’s episode we share part 2 of our interview with Mike Wood, detailing his experience taking a personal sabbatical, how he spent the time off, and how he orchestrated his next career move.

Original Recording Date: 02-24-2022

Mike Wood works for Microsoft as Technical Program Manager of the Commercial Software Engineering group. This is an enablement organization inside Microsoft, working with and coding with some of Microsoft’s largest customers to solve problems on the Azure platform (cloud and edge). Catch part 1 of our interview with Mike in Episode 168.

Topics – A Personal Sabbatical, Deciding What to Do with the Time, When Organizations Value People, Discovering What You Want, The Resume Gap, Career Flexibility and Parting Thoughts

3:07 – A Personal Sabbatical

• One of the acquisitions prompted Mike to take some time off (most recent one).
• Mike was working for a company called SentryOne, a company that made monitoring software for SQL Server, which was acquired by Solarwinds (a much larger company). The acquisition is detailed here.
• This was during the pandemic. SentryOne had to furlough some people as well, making stress levels rise because the company was small enough for most employees to know all other employees, even across departments.
• Then when the acquisition started, the team was told Solarwinds wanted the engineering talent and the technology to incorporate into the greater Solarwinds portfolio.
• Mike wasn’t concerned about losing his job but more about what he would do as part of Solarwinds.
  • At the time he was the Site Reliability Engineering Manager at SentryOne, a team that became a little smaller pre-acquisition.
  • The team shrank even more post-acquisition due to turnover.
  • This became very stressful, and it was not clear what Mike would be doing long-term for the company.
  • Things began to pile up. He needed to take more time off than what he would be allowed to take and wasn’t sure it would be the right place for him to return to after the time away.
  • This would not have been somewhere he would have applied to work.
  • Mike approached it from the standpoint of wanting to take more time off than he had vacation and take it immediately.
• The decision to take time off was not a sudden decision but required much consideration up front.
  • It became a family discussion. This was about a year before the time of this recording.
  • During the pandemic, Mike and his wife started taking walks together around the neighborhood after work to deal with stress.
  • His wife is a teacher who was working in a noncontinuing contract (only guaranteed employment for a single school year with no guarantee of another job the following fall). Mike needed to get out of what he was doing, and he was trying to determine feasibility. This was a conversation that took place over many walks.
  • Mike and his wife had made some good financial decisions. SentryOne made their employees part owners in the company, and employees made some money in the acquisition.
  • Mike and his wife had been saving money to do a project for their house.
  • They talked about how long they could sustain their current lifestyle (without raising it) with Mike not working for a while (a personal sabbatical).
  • The original plan was for Mike to take a month off and do no job searching or have discussions about it, which means he would be out of work for more than a month at least. At the end of that month, Mike would start looking for what’s next with the goal to have a job within 3 months…which turned into 6.
  • The extended time period was partially due to specific things Mike was looking for and being confident he could make money on the side if needed.
  • Mike’s wife got a new contract teaching (this time a continuing one) which paid the bills during this time. At this point it became less of a rush for Mike, and he was able to pursue what he wanted to do.

9:31 – Deciding What to Do with the Time

• Before taking the sabbatical, Mike started writing down things he would do during the time off, which turned out to be a mix of things.
  • He renewed a certification in the first month and ended up racking up a couple more certifications along the way.
  • Mike spent more time with his family, but he’s worked from home for over 8 years now. More time with the family was Mike being available to do something when his son got home instead of 1.5 hours later.
  • A large portion of this was during the summer, so his wife was off work as well. They took a trip to a small cabin and even spent time in Columbus but kept trips to a minimum.
  • Mike had a list of things that needed to be done around the house.
  • One of Mike’s hobbies is amateur radio, and one of the things he likes to do is called Parks on the Air. There are activators that go to a local park with their radios. There are people called chasers who are trying to get Parks on the Air contacts, and you get points for each role.
    • Mike spent some time trying to hit as many parks as possible and visited others here and there during the time away.
  • He also played a lot of video games.
  • Mike spent a decent amount of time thinking about what was next for him. After the first month he started asking himself…
    • Where do I want to work?
    • What type of company do I want to work for?
    • Do I want to continue in site reliability (his most recent work)?
  • If you want to change what you do and you put on LinkedIn that you’re looking for jobs, it seems like you are pigeonholed into the most recent thing you’ve done.

13:26 – When Organizations Value People

• Mike did spend a lot of time thinking through what he wanted to do, which was extremely helpful. He was able to have conversations with many people about what they did.
• After having interviewed at Microsoft multiple times over the years and not making it (learning something every time), Mike thought it might be the right time to try again.
  • Mike had someone encourage him to interview with Microsoft back in the GA Sullivan days.
    • "I’m not saying you have to leave. Just go interview. Go and have that experience and know what that experience is like to interview with a large company."
  • Mike wishes he would have listened to that person back then, stating he would have learned all the lessons from the last year.
  • The interviews in the past at small companies were very different. Some interviews early in Mike’s career were very technical.
  • Interviewing at a large company was very different. These companies have their own process you need to learn and understand.
  • Mike was advised to get informationals. These are not formal interviews but are with hiring managers / someone at Microsoft about what their group does.
    • At Google these are called champion calls.
  • During the calls you talk about what the job is like, what it is like to work at the company, etc.
    • Most of them led Mike to the conclusion that the role may not be a good fit.
    • But during these calls, the person from Microsoft would ask what Mike wanted to do, what he did in the past, and what his interests were. At the end of the call, most of the time, the person recommended he talk to someone else inside Microsoft.
    • Through this process (doing informationals), Mike found out about a number of roles inside Microsoft that he might not have found on the careers website.
    • This sounds somewhat similar to the LinkedIn Live career events VMware has done. See Episode 162 for more detail.
    • Nick loves the fact that the people Mike spoke to in the informationals wanted to help connect him with people who could share more about what he might want to do (almost like they could spot and enable talent).
    • This speaks volumes to Mike about how they (Microsoft) value the person. If you have companies that recognize what a person is good at and what they want to do, the employee will be more engaged.
• When Mike was at SentryOne he was a product manager for a couple of years and felt he had become less technical, which he did not like.
  • Mike told his manager about this, who was super supportive.
  • It almost got to the point where he knew there was no path for him, and the folks at SentryOne were supportive of even that decision. If Mike felt leaving was the best path, people at SentryOne could help him make connections even outside the company.
  • Mike had Azure experience from a previous role and was offered a role at SentryOne as a lead cloud engineer. This turned out to be a great role for Mike and led him into the site reliability engineering position mentioned earlier. He and his team got to help build up the SaaS offerings at SentryOne as well as processes around it. Building all of this from scratch was a great learning opportunity.
  • The company realized if they put Mike in the position it will work out well. Having companies that realize this and not just think of employees as cogs is refreshing.
  • John says it’s possible you could learn a lot as a cog in the company’s wheel, but in our careers we need to decide if it’s ok for the company where we work to treat us like cogs. Different points in time, mindsets, and personalities influence our decisions. Being a cog may be exactly what you are looking for to gain specific skills or exposure. And that is ok.

21:45 – Discovering What You Want

• Mike references Brian Prince, someone who was a developer evangelist when they first met. Brian said every year right around Christmas he would take a day off to think through whether he would recommit another year to his company or look elsewhere.
  • Are all the things I am looking for being met?
  • Am I excited about what I am doing?
  • Or do I need something else?
  • Am I getting what I want out of this?
• Brian gave a great presentation with career advice at one point, and Mike took much of it to heart.
  • Mike does spend time thinking about whether what he does is what he wants to continue to do.
  • During the sabbatical this came into heavy focus. You start writing down a list of the amount of travel, how much you need to make, and a number of other things.
  • In the software industry Mike feels the majority of us are blessed with decent / better than decent wages. Though salaries in other areas may seem huge, Mike lives in the Midwest where the cost of housing is nowhere near what it is in other areas.
  • To some degree it comes down to whether you’re happy with what you’re doing, what you want to get out of it, if there is some part you want to share and give back, etc. There is a lot of leeway in at the intersection of a fulfilling job and making what you need to make.
    • Perhaps you would give up some extra pay for certain things you want.
• By the time the sabbatical came, Mike had been in his career for over 20 years. Some things he already knew in terms of what he wanted (i.e. very clear).
  • There was a maximum amount of travel Mike would not surpass (was not worth it to him due to commitments outside of work).
  • He wanted to be hands on technical wherever he landed.
  • Mike looked back at all the places he had worked and at the things that worked out for him as well as those which did not. This allows you to adjust what you want over time.
  • Some folks who found out about Mike’s sabbatical were slightly freaked out by it (sticking to the concept of it being easier to find a job when you have one already).
    • Mike understands not everyone has money set aside to take a break like this.
    • He also had an extremely supportive wife throughout this whole process.
  • Mike already had the build up of the things in the past that shaped what he wanted from a job / company, but the break allowed him to truly focus on exactly what he wanted.
    • The informationals at Microsoft steered him into the right organizations.
    • There may be many openings at a company like Microsoft, but there are not that many if you’re targeting a specific organization within. That makes the cycle longer.
    • John says this is the sniper approach and not shooting skeet with shotguns.
      • The best time to be recruited for a better job than you have now is when you’re in a job that you are happy with, which is very different from the best time to look for a job being when you have a job.

29:27 – The Resume Gap

• Having taken a sabbatical and looking for a job, the hiring manager knows you’re not working because they will ask where you are working now.
  • You need to be cautious here as it will affect your ability to negotiate.
• If you have a job and you really enjoy it, it’s easy to say thanks but no thanks.
• When you don’t have a job you don’t want to be in a position of taking anything the company will give you.
  • Mike felt like he had a good network built up over the years so that he could find something (even if it was side work) to pay the bills until he could find something else.
  • Working for himself likely would have made Mike uncomfortable since he is not a great salesperson. He also did not want to have to mess with health insurance and other things (a barrier to those who work for themselves).
  • The 1099 hourly rate is much higher.
  • Mike mentions Michael Eaton, someone who was an independent contractor who was doing a talk on the pros and cons of being an independent consultant (marketing, selling, admin stuff, etc.).
• Because of the pandemic, most everyone in the interview process was understanding of Mike’s needing to take time off.
  • Microsoft as a company did a lot around wellbeing for its employees, providing extra wellbeing time off in addition to vacation days.
  • People understood the time off without Mike having to explain the acquisition process that led to the sabbatical.
  • If Mike had to interview again, he might have a different viewpoint on needing to explain the 6 month resume gap.
  • Mike was more afraid that the gap would affect his ability to negotiate. He had to make it extremely clear to the employer that he decided to take the break on his own, that he had many options, and that he had plenty of money to sit on to continue his search.
    • The money set aside for his search was finite, but he needed hiring managers to know he wasn’t desperate.
  • John thinks job changes during the pandemic will not be something people bat an eyelash at moving forward.

35:51 – Career Flexibility and Parting Thoughts

• Mike says he went through the numbers and how much the family paid each month, how much was set aside for their deck project, and determined how many months they could go without getting to a desperation point.
• Keeping finances in order creates the flexibility. Even if you are working at a great company, you don’t know what might change.
  • If your lifestyle increases with every raise you will have no margin for error.
  • People might have an emergency fund or a dream fund, and sometimes the dream becomes taking a 6 month sabbatical. Only financial cushion allows for this.
  • There are different levels of a bad situation. The financial cushion can enable career flexibility if needed.
• Mike is blessed in that he and his wife think of money the same way. They definitely spent a lot of time building wealth.
  • Mike wishes he had been told early on to max out his 401K and other advice. He got carried away with credit cards, for example. Lucky for him he was able to work overtime and pay this off before getting married.
  • Mike wishes he had been saving earlier in life. But since that debt payoff before getting married, Mike has continued to think through how to save and how to create the rainy day fund.
    • Some people say you need 6 months of money sitting around just in case to be paid for any sort of emergency.
    • Mike’s advice would be talk to a financial advisor as to how best to do this to get to the money easily but also so it is protected.
• When Mike and his wife got married, his wife had investments at Edward Jones.
  • They went to have some conversations with the local Edward Jones agent, who they still use today.
  • Mike used to only contribute to his 401K what the company would match, but he was not maxing it out.
• One of Mike’s new colleagues is super into stocks and leveraging them for buy, sell, and many other options and educated Mike. This person has a higher risk tolerance than Mike.
  • Mike recommends finding a resource like somoene at Edward Jones or doing the research yourself.
  • John says Personal Finance for Dummies helped him a great deal. He thinks a book like that or something similar is helpful.
  • John also had parents who taught him how to manage money, but that isn’t everyone.
• It feels like we’ve only scratched the surface on Mike’s career experience. We need to have him back at a future time to go deeper on some of his transitions.
• If you’re considering a sabbatical, make sure to take the time to think it through!
  • Don’t treat it as a big vacation. Going into it you need to know what your goals for it are.
• You can find Mike on LinkedIn or Twitter.

Contact us if you need help on the journey.