10 Strategies to Reboot Your 50-Plus Job Search

So you’ve been struggling in your job search and you’re starting to lose hope. For many 50-plus job searchers, there’s uncertainty about where to start. For others, there is a lack of confidence around branding. And for others, there’s a lack of experience navigating the online job search terrain. All of this can drag out the search, leaving a 50-plus job searcher discouraged. If your senior-level job search doesn’t seem to be working out, it’s time to try a new strategy. In this blog post I’ll share some proven strategies you may not have considered for rebooting the job search in your 50’s.  

How to move past roadblocks in the 50-plus job search

If it’s been a while since you searched for a job, you might be learning the hard way that it’s tougher than you expected. This is normal. Getting stuck in a job search rut is easy to do and very common amongst the majority of senior job searchers I meet. If you’re not careful, or aware of the ways around this rut, your job search can take significantly longer. It can also take a hit to your mental game. This will mask your ability to see a light at the end of the job search tunnel. And of course all of this may end up hurting your confidence. If this sounds like you, don’t worry. The most important thing to remember here, is to hit reset on the search and keep moving forward. If you’re finding it difficult to land a job, the first thing you must do is: stop and regroup. Spend a few days revising your job search plan, and then move forward. There are several proven ways to produce results in the job search. Here are my recommendations for you. If you are concerned about ageism blocking your efforts, check out this blog post on how to eliminate ageism from your search.

1. Put the online job search on hold

You may be surprised to hear this, especially since online job boards are the best place to find a lot of jobs. However, it’s important to hear. Sitting behind your computer screen all day is NOT a strategy. It can be more of a mental strain and motivation drain than anything else. Therefore, I recommend putting the online search on hold. Then, it’s all about trying new strategies to shake things up. They say that the definition of insanity is doing the same thing over and over again, and expecting different results. Well, take this little nugget of wisdom into account. Commit to making a big change in your job search. You don’t have to abandon online job boards completely. You just have to put them on pause until you’ve tried these other search strategies. You may also find yourself in a more positive place after taking a break. Trust me, it works!

2. Try networking to find new opportunities & forge connections

One job search approach that is neglected by job seekers at all levels, is networking. Networking is by far the most effective job search strategy. And it happens to also be the best strategy for job searchers facing age discrimination. Because you’ve been in your career longer than your younger colleagues, your network is significantly larger. This is great news for you! Networking boasts tons of benefits for your search and it will open up doors quicker than sending online applications. There are several easy strategies for effective networking. The most effective one for you, will be the informational interview. Take a few weeks off of the online job search, and focus on networking. I guarantee it will start to really move your search in the right direction. If you have anxiety about networking, you will want to read this blog post on how to overcome it.

3. Consider working for free and enhance your resume experience

Working for free may sound crazy since your goal is to land a paying job. But, in a competitive hiring environment, working pro bono works. This is especially effective if you have a connection at a startup or non-profit who is in need of some extra help. Even approaching an overloaded VP at an established company, to pitch a pro bono project, can be appealing. The key here is using your gifts and skills to fill in the gaps at an organization in need. Great with analytics? Offer to conduct marketing analysis aimed at increasing customers. Targeting a career in writing? Offer to produce blog content or even launch a blog for a small business. You may be vey surprised at how receptive organizations will be towards your offer. If you are planning to go this route, be sure to prepare a professional presentation or proposal as part of your pitch.

Working for free can benefit your job search in several ways. First, you will be gaining real-world experience to add to your resume. If you are trying to make a career change, pivot or reentry move – having some part-time or project work relevant to your target industry, is looked upon favorably by hiring managers. This resume addition will brand you as someone with experience in your target field – which is always a good thing. Second, if the opportunity goes well, you may end up with a job offer. You don’t have to work for free forever. However, if you’re in a dead-end search, this could be just the thing you need to create new results. It could also turn into a fast-track for landing a job.

4. Be open to less than ideal opportunities

Contract or temporary work is another great way to get your foot in the door. It may not sound ideal since you are trying to land a full time job, but it does have the potential to turn into one. Many well-known companies want to test your fit before they commit to hiring. Therefore, some full-time roles, start out as contract roles. Once the employer gets a taste of how you work, they will be more open to the idea of bringing you on full time.

If you are approached about a contract role, do your homework and learn more about the organization. You may find that contract work is how this particular company hires full-time salaried staff. Be sure and ask about the potential for full-time salaried roles as a continuum to the contract work. If the company has done this before, they will let you know. Don’t ever rule out contract work. Contract roles may be a good place for you to restart your job search. Contract roles can also be great for networking since you’ll be working alongside more established employees.

5. Turn volunteer work into a paying job

There are tons of benefits to volunteering while in the job search. If you’ve been in a long job search or are re-entering the workforce after many years away, volunteering will fill your resume gap. This will ensure your skills aren’t becoming rusty from not working. Volunteering is a great opportunity to raise your hand for jobs and gain real-world experience. Volunteering will also allow you to top up the transferable skills needed to gain experience for your target job. These new skills make great additions to the Skills section of your resume. One of the biggest benefits of volunteering is the opportunity to network your way into a paying job. Of course this isn’t always possible. Much of your ability to turn volunteer work into a paying job will depend on the company situation. It may also take time. However, it is a possibility that exists and my clients have been able to do this successfully! The most important thing to remember when starting volunteer work is to perform your work well, and build relationships with everyone you meet. If managed correctly, the relationships you make will help you navigate the internal working of how to get hired.

6. Attend free job search workshops

Many career coaches or experts are hired by local venues to teach workshops – usually free to the public. For example, one of my local libraries brings me in every month to offer workshops or job support groups. In these workshops, I’m sharing all of my knowledge with the attendees for free. Many attendees find it extremely valuable to be able to ask questions specific to their situation. And of course, I’m there to help in any way I can!

These job search workshops are also valuable for networking. At these workshops you will be surrounded by other people experiencing the same job search challenges as you. Many of these folks are more senior professionals who may be willing to open their respective networks to you. I often find people connecting during and after my presentations to exchange suggestions/offer help. So in addition to receiving free coaching, you are also receiving an expanded network and potential job leads. Even if you don’t feel like going, I would encourage attendance. You never know who you will meet or what insights you will gain. Start by visiting your local library website and check out the events page. Or find other venues nearby that host business/career speakers.

7. Attend industry-related events

In addition to job search workshops, attend any and every industry-related event in your local market. Interested in a career in Finance? Attend every finance workshop, networking event, conference, etc. These industry events are where your key networking contacts will be hanging out. You might end up sitting next to an HR person or hiring manager at a great finance company. You also will increase your chances of finding new networking leads. When you fish, you have to go where the fish are. And these types of events are where your fish will be! Check the local paper, industry association websites, or eventbrite for starters. These are the places industry-related events will be advertised. Then, start to attend.

8. Volunteer at industry-related events

The only thing better than attending an industry-related event, is volunteering at one. If you happen to live in a market that attracts large industry events, and you have some lead time to enroll as a volunteer, this is an excellent way to make new connections. Many industry events will open up volunteer opportunities in advance. If you do not see opportunities advertised, search the event or association website for a point of contact. Send an email inquiring about opportunities to help during the event. This will allow you opportunities to rub elbows with folks who have deeper involvement in your target industry. It will also speak highly of you for taking the time to volunteer. It may also afford you the opportunity to attend a pricey industry event for free!

9. Network at the top of the food chain

The standard networking contacts you’ll be targeting include, recruiters, industry peers, and company insiders. These are all great contacts that you’ll need to engage. But you might also consider networking with senior professionals in your target industry. When you network with someone at the top of an organization, that person has the power to pass orders down the organization. Ideally the person you network with at the top, likes you so much that they are asking HR to schedule an interview. This kind of request to HR from a senior stakeholder is powerful.

Of course not every senior executive will make time for you. However it’s certainly worth a try. Find someone in the C-suite of your target company. Send a Linkedin connection request and follow up note. Make a brief introduction and share how you admire their success. Then ask for a brief phone call or in-person meeting to learn a bit more about how they were able to achieve this. If you are earning more than 6-figures, you will want to also network with these top executive recruiting firms.

10. Find an accountability buddy to help with motivation and unlock job leads

As you network, you’ll want to keep an eye out for potential accountability buddies. Specifically, aim for someone who is in a similar industry or job search situation so you can help each other reach your goals and stay committed to the search. However, a senior professional, in an unrelated industry can also be valuable. A buddy will want to see you succeed and therefore be more open to sharing contacts and job leads. They may also serve as a faux career coach since they have likely navigated their own career path including interviews, offer negotiations, etc. The goal is to find someone who can offer encouragement and guidance as you try to navigate all the moving pieces in your network.

Combine multiple search strategies to land your job quicker

These 10 different approaches should be just the thing you need to shake up your 50-plus job search. If it sounds overwhelming, just start with one. Many successful job searchers find that a combination of several is the best mix. In order to find the right mix, just start moving forward with one and then incorporate another. If doors open for volunteer or contract opportunities, move forward. If doors don’t open, don’t get discouraged. Just choose one of the other approaches shared here!


If you’re hoping to reboot your 50-plus job search and reduce age discrimination, check out our ageism-busting resume services. Our master resume writers will provide you with a custom resume strategy phone consultation, ATS and keyword optimized resume, and tailored resume that speaks to your strongest career accomplishments and value – everything you need to feel confident, navigate the job search successfully, and put your best foot forward as a 50-plus applicant.

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