Overcome your reservations and start your encore career

Working part time or freelancing seems like an answer to many Boomer’s needs. It can provide them with some supplemental income, keep them active and engaged, and help them to maintain their skills up to date or learn new ones. Many would love to do some part time work to pursue their passions or interests.

For many Boomers working part time or freelancing at the end of their career also makes sense in light of the Social Security benefits. If you are able to supplement your savings with part time work and delay drawing your Social Security benefits until you are 70, you will receive maximum benefit at the time you need it most.

Surprisingly though Boomers are not actively exploring these options. Here are some often used reasons why they are not there yet.

I do not have the right skills to be a freelancer.

It is common to think that freelancing is limited to either technology, creative design or writing. While these fields are most advanced in terms of using freelancers, there are plenty of other opportunities for Boomers. Many companies want freelancers who can work outside of the office and online doing jobs that require just basic computer skills like sending emails and filling in forms. They are also open for freelancers to perform administrative tasks, doing accounting, managing customer relations and many other tasks. In addition, there are plenty of inexpensive online training platforms such as Lynda.com or EDX.com to help you stay competitive.

I do not know how to market myself

Traditional ways of looking for a job do not work when searching for a part time or freelance work opportunities. Unlike applying for a defined position at a company, freelancer has to convince a prospective client to trust them with a specific project or a task that has a defined end date. There are simple steps you can take though to learn how to change your personal marketing. Here is a simple list that can help you get started.

I do not if I will make enough money

When working full-time for a company, you’re paid a fixed salary each month. You also hopefully got medical insurance, paid leave and other perks. Freelance jobs do not offer this certainty. Amount of money earned directly dependent on your rates and amount of time spent working. In order to make it worth your while, you will need to be able to negotiate reasonable rates for your services. When starting down this route, there’s nothing wrong with low rates, as long as you have a plan on how to increase them as your experience and portfolio of projects grows. There is also an opportunity to provide additional services as you build relationships with your clients and they see that you deserve higher pay.

I cannot manage my time

Working 9-5 job provides stability around which it is easy to plan your day. You are in the office or job-site with little to interfere with your duties. But when you work as a freelancer, you may be exposed to unpredictable spikes in work or distractions during what is supposed to be your working hours. Freelancing offers great flexibility to manage own time and effectively be your own boss but without some discipline, it is easy to lose track of your project and end up upsetting your clients. Luckily there are many ways and tools to help you manage your time. You can take your work anywhere you go, leverage mobile communications to stay in touch with your clients and rely on on-line calendaring such as Google Calendar to make your daily schedule. Freelancing is about finding the work/life balance, so think about how much time you want to allocate to work and stick to your schedule.

I do not know where to look

Although there are several on-line freelance platforms, any Boomer that signs up there will be faced with stiff competition from offshore freelancers that provide services at a very low cost. Most of the services offered are technology related. It may not seem to be worth it to do work for $5 an hour, which is where a lot of services are priced today. However, Boomers with the right skills should look for platforms that focus on more specialized skills.

I cannot handle pressures of working for a client

If you have not worked part time or as a freelancer, you may be concerned about the added pressure of dealing with clients. Freelancing will indeed expose you to potentially unreasonable demands and rejections. Instead of hearing the news from your manager though, you’ll be hearing it directly from the client that pays your bills. Whether it’s a rejection (they’re the hardest to take), an unreasonable demand or just a disgruntled client, you’ll need to have a way of handling the situation. But if you keep your emotions in check, these situations can present an opportunity to turn a bad situation into a win. Boomers have great soft skills such as listening and understanding. When the situation is difficult, they can rely on their past experience and find ways to resolve conflicts. Clients will appreciate a mature approach and will trust you more in the long term.

Secret to Success

The secret to succeeding as a freelancer is to find what you enjoy doing and treat it as a business. You will be the CEO of your freelance company – how cool is that? Stick to the work ethics that you developed to during your office-going days, think long term, be determined and you’ll be fine. As a reward you will make money, stay active, meet new people and have flexibility to manage own time. Remember, we are here to help you on this journey.


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