Thinking of working for yourself? How to tell when you’re ready

Turning your side hustle into a full-time job is an exciting career move that you should only take if you can answer these 4 questions with confidence.
By aha insurance - Apr 9, 2020

At aha insurance we continually explore ways to stay in control of all aspects of life – because we know life is about more than insurance. In our Work Matters series we talk about staying in control of your life and reaching your #careergoals. Control feels great!

You are not alone if you dream of leaving your conventional 9-5 job to go into business for yourself. The thought of being able to make your own hours, choose who you work with, and directly benefit from your talents and success is very attractive to many professionals.

However, while working for yourself can be extremely rewarding, it can also bring forth new challenges. Your ability to manage and motivate yourself are important, but let’s take a deeper look into 4 critical predictors of success you should master before transitioning towards self-employment.

Do you have a developed network?

Networking is important for anyone looking to build a successful career, but it’s even more crucial (and often difficult) when you can’t rely on an employer and coworkers to help you make professional connections. Having a large number of LinkedIn connections is great, but you need to cultivate mutually beneficial one-on-one relationships to help you weather the unique challenges and hopefully stave off the potential dry-spells that can come with self-employment.

Before you consider working for yourself, you should build a strong, wide, and diverse network of relationships that can help you grow your business and provide you with the professional development you need as both your own boss and employee.

  • Maintain your current professional relationships
  • Share your time and expertise generously
  • Thank everyone who helps you out and show your appreciation by returning the favour at an appropriate time if you can.
  • Network outside your industry as much as inside of it. There’s valuable networking opportunities everywhere you go, and it’s a great way to practice building your networking confidence.
  • Organize your contacts’ information, collect business cards, and record some basic details with each new person you meet.
  • Follow up with new contacts like you would after a job interview. Send your new connections a follow-up email reintroducing yourself and thanking them for their time.
  • Leverage social media and other online resources like Meetup and Eventbrite.
  • Prepare and rehearse your elevator pitch to introduce yourself and your services so you can be as relaxed and confident as possible during networking events.

Working for yourself is rewarding, but it can also be isolating and less prosperous than you would like, if you don’t take time to grow and nurture your existing networks. Your networking practices are how you market your services to clients and other professionals who can bring you business.

Are you solving a specific problem?

Networking is how you market your services—and what factor makes your services significantly easier to market? Your services’ ability to solve a specific problem. According to the founder of AllTopStartups, Thomas Oppong: “Focus on building a must have not a nice to have product.”

You need to clearly define the problem that your business will be solving and make sure your future clients will agree that it’s a crucial problem they experience. Do your research and speak with as many potential future clients as possible to get a better understanding of what services you can offer that they can’t function without.

Many people in your field may be offering similar products or services. Long before you quit your current job, you need to make sure that the solutions you are offering your clients are measurably more innovative and efficient than those of your competition.

What’s the state of your financial cushion?

This is an important question because even if you have all the skills, knowledge, experience, and non-financial resources in place to start working for yourself—not being financially prepared can leave you in a stressful situation.

According to Erin Lowry from Broke Millennial, having a lucrative side hustle is the best way to prove to yourself that you’re ready to leave your current job and become your own employer. If you can live solely off of the income generated from your side business and stash your regular paycheck away for savings – that’s an excellent indicator that your business is lucrative.

Maybe when you run the numbers, you’ll find that devoting yourself to your side business full-time could be as or more profitable than your current position if you devoted 100% of your working hours towards working for yourself.

Of course, to prepare for the likelihood that self-employment initially pays less than your old job, you should ideally have 6 months worth of living expenses saved to help your career transition survive any unexpected losses. Having enough savings is also necessary because you’re going to need to set aside a percentage of your earnings for your tax bracket.

Here are some other important questions about the strength of your financial cushion that you should consider:

  • Do you already have clients that are ready to send business your way once you transition to working for yourself full-time?
  • Will your finances allow you to comfortably wait 2-3 months for your first client to pay for your services?
  • Do you have a business account in which you’ve already deposited a healthy amount of earnings from the side hustle you’re turning into your full-time hustle?
  • Can you afford to purchase business insurance if necessary?
  • Can you afford additional health insurance for yourself and your dependants? Keep in mind that OHIP doesn’t typically cover dental care, vision care and prescription medications.
  • Will you still be able to save 10-15% of your income for your retirement?

If you can confidently answer yes to these questions, you’re likely financially prepared for the initial expenses that working for yourself requires, allowing for the time you need to grow your business at a realistic rate.

Is your work portfolio ready to impress?

Even though you’re not looking to apply for a job in the traditional sense, you still need to showcase your skills and drive to attract potential clients and customers. Make sure your portfolio is updated and polished before you head out to be your own boss.

Your portfolio should include

  • Your resume, tailored towards your line of work.
  • Biographical information that helps you make a personal connection to your potential clients. Don’t be afraid to let your passion for your work and helping clients shine through while you talk about your career journey.
  • Testimonials, reviews, and recommendations from employers, clients, customers, teachers, or any other relevant authority. Just like with a standard resume, including contact information for these references is important.
  • Proof of your education, credibility, and commitment to ongoing learning. Here you can include proof of your educational accomplishments and professional licenses as well as information about your participation in courses, workshops and seminars in your field.
  • Samples of your work accompanied with descriptions and results. If the work you’re showcasing is tied to a particular achievement or award—like top marks, a promotion, or an employee of the month designation—don’t leave that out!

Samples of your work are really what separates your portfolio from your resume, so take extra care when you design the layout and content of this section. If you don’t have samples of your work to display because you are just starting out, or your work for previous employers is proprietary, then create work samples specifically for your portfolio that highlight your key skills and talents. You can tailor these work samples to a specific client you’d like to work with or an imaginary ideal client.

Even if you’re not a photographer or videographer, including multimedia like photos and videos can help showcase your work in an engaging way. Check out this article from The Muse for some inspiration on how to visually present what you do best.

You’ll probably want to invest in making your portfolio available online, especially if you’re actively looking for new clients. The good news is you have a host of portfolio website builder options that make building a great looking and performing portfolio more accessible than ever before.

Your portfolio will need to be updated on a regular basis even after you start to land those desirable clients in your field. Once you have these key aspects of your portfolio ready to present to your network of potential clients, you’ll be one big step closer to successfully working for yourself.

Now that you’ve reviewed what you need in order to successfully work for yourself: Are you ready? Or do you need to take some more time to prepare before you take the plunge? Remember that the journey towards self-employment can be long, but worth the extra effort. After all, working on developing these 4 aspects of your career will make you more successful whether you ultimately decide to work for yourself or land your dream job working for a larger organization.

aha insurance is Canada’s first car and home insurance brokerage to offer a fully online customer experience. Customers can purchase and manage their car and home insurance online in minutes from the convenience of wherever they are. This puts customers in complete control, and control feels great.