Tag Archives: encore careers

Seeking Financial Freedom? 9 Tips for Escaping the Traditional Job

Photo by Juan Mendez on Pexels

Discover practical strategies for achieving Financial Independence beyond the confines of a traditional job.

This article presents expert-backed advice on creating multiple income streams and aligning work with personal goals. Learn how to leverage your skills, build value-based income, and take concrete steps towards your vision of financial freedom.

  • Leverage Your Skills for Side Income
  • Transform Evenings into Venture Capital
  • Build Value-based Income Streams
  • Adopt a Side Hustle Mindset
  • Future-Proof your Professional Value
  • Align Work with your Core Purpose
  • Build a Financial Foundation first
  • Get Specific about your Goals
  • Cut Expenses to Create Options

Leverage your Skills for Side Income

In today’s evolving job market, many professionals find themselves tethered to traditional 9-to-5 roles: secure, yes, but often creatively or financially stifling. The desire for financial freedom is not just about escaping the office; it’s about reclaiming time, purpose, and the ability to design life on your own terms. We’ve worked with countless individuals who once felt exactly this way: stuck, uncertain, but ready for a change.

If you’re feeling trapped in a conventional job, the most important first step is to acknowledge that your desire for more isn’t selfish: it’s strategic. Financial freedom isn’t just about money; it’s about choices. And that journey starts by understanding your own value in the marketplace.

Step 1: Audit Your Skills and Strengths

Take stock of what you’re naturally good at and how those skills can translate into high-demand, high-autonomy industries. Digital skills like coding, copywriting, digital marketing, or consulting are especially valuable in today’s freelance and remote economy. Ask yourself: If I had to solve someone’s problem for a fee: what could I offer today?

Step 2: Start a Low-Risk Side Income Stream

This doesn’t mean quitting your job immediately. Start small: freelancing on Upwork, tutoring online, offering resume reviews, or starting a blog or YouTube channel around a niche you know well. Build proof of concept without jeopardizing your current income.

Step 3: Invest in a Career Coach or Mentor

Working with a coach can help you shortcut the confusion. We help clients identify the right path forward based on their lifestyle goals, not just job titles. Our structured guidance has helped people launch side businesses, shift into more flexible roles, or double their income by making strategic pivots.

According to a 2024 report by LinkedIn Workforce Insights, over 60% of professionals under 40 are actively seeking roles that offer greater flexibility and autonomy. Additionally, Harvard Business Review found that professionals who pursue “career portfolios” — multiple income streams from various skill-based services — report 43% higher job satisfaction and 31% faster income growth than peers in static roles.

Feeling stuck isn’t the end of your story: it’s a signal. A signal that you’re ready for change. We believe that financial freedom isn’t just for the lucky few—it’s for anyone willing to make bold, informed moves. Miriam Groom, CEO, Mindful Career inc., Mindful Career Coaching

Transform Evenings into Venture Capital

If you’re feeling stuck in a traditional job and craving more financial freedom, you’re not alone: and you’re not broken. That restless feeling? It’s your internal compass telling you that what you’re doing no longer aligns with where you want to go. My advice? Don’t silence it: study it.

The most powerful first step I ever took was treating my evenings and weekends like venture capital. Instead of doom-scrolling or complaining about my 9-to-5, I built skills that made me valuable outside of it. I didn’t quit blindly. I audited my strengths, explored high-leverage models like consulting and digital products, and tested small bets until one clicked. It was less about passion and more about leverage: where can I help people, solve problems, and get paid well for it?

If you’re after financial freedom, don’t chase quick wins. Chase agency. Build something that compounds. Start by learning one monetizable skill: something you can offer tomorrow. Package it, test it, refine it. You don’t need to be loud online or have a business plan that wins awards. You need to take the first step: and then the next.

What I’ve learned from growing multiple businesses and coaching founders is this: freedom doesn’t arrive fully formed. It’s built in the margins before it becomes the main thing. So if you’re reading this wondering if it’s too late or too risky: it’s not. Your current job might pay the bills, but it doesn’t have to define your ceiling. John Mac, Serial Entrepreneur, UNIT

Build Value-based Income Streams

If you feel stuck in a traditional job, it’s because your income is locked to your hours. Financial freedom begins when you earn based on value, not time. The fastest path is building a side income that proves you’re worth more than your salary. That means selling a skill — marketing, coding, design, sales strategy — directly to people who need results, not resumes.

I replaced my paycheck by packaging my experience into targeted offers. One client became two. Two became four. The process wasn’t complicated. I identified a problem, built a simple solution, and sold it. The first $1,000 didn’t change my life. It changed my mindset. From there, scaling was execution, not hope.

Most people stall because they’re waiting for the perfect idea or ideal conditions. Neither exists. Start by solving one problem for one customer. Build income that’s not tied to your boss. Cut costs, track results, and reinvest profits. Don’t romanticize the idea of freedom. Make it measurable. Give yourself a deadline to match and then exceed your job income.

You’re not trapped. You’re unproven. The solution isn’t to quit. The solution is to validate your value outside the structure you’ve been conditioned to depend on. You move forward the moment you stop waiting. Steven Mitts, Entrepreneurial Coach, Steven Mitts

Adopt a Side Hustle Mindset

Traditional jobs are great for many reasons, but I completely understand. I was stuck in a normal or traditional 9-5 job, and the only thing I was dreaming about was freedom. This feeling is more common than you might think, so anyone who is experiencing it, you are not alone. The best advice I can offer is to change your mindset, more specifically, to adopt a side hustle mindset.

Think about what you currently have in your job: stability, which hopefully provides a decent income. This is a huge asset. Use this stability to your advantage; don’t think of it as a cage, but rather as your investment stream to financial freedom. Then, make a list of the skills you have, things that you like (passions) that could be monetized, or if you’ve noticed a problem that many people experience and you may have the solution, it could be your golden ticket.

Once you have your idea, don’t quit your day job. Dedicate a small but consistent chunk of your time each week to your new adventure (5 hours to start with will do). When it comes to the steps I’d recommend you take, there is only one: validate your idea. Do your research; you don’t want to waste countless hours on something that is already thriving. Once validated, begin your journey. Draw up a business plan, get a name (register it), open a bank account (do not use your personal one), then start. Take that first bold step. It is incredibly exciting, and it can induce a whole heap of fear, but you will never know if you don’t take it.

My encouragement is this: every great entrepreneur started with a tiny step. No one jumps into success; it is built from the ground up. Aiden Higgins, Senior Editor and Writer, The Broke Backpacker

Future-Proof your Professional Value

Honestly, the biggest shift for professionals feeling trapped isn’t just leaving a traditional role: it’s strategically future-proofing their value. Research shows 65% of workers who feel ‘stuck’ actually suffer from skill obsolescence, yet those who dedicate just 5 hours weekly to learning in-demand capabilities like automation fluency or data-driven decision-making see a 47% faster transition to higher-paying, flexible roles.

Start by auditing daily tasks for automation potential: this reveals immediate efficiency gains and highlights valuable skills to develop. Platforms offering certified, applied learning in operational tech turn that insight into tangible leverage. That frustration? It’s actually a compass pointing toward untapped potential.

Financial freedom isn’t about escaping the grind; it’s about equipping yourself to command the work that matters. Every expert was once someone who decided their growth couldn’t wait for permission.Anupa Rongala, CEO, Invensis Technologies

Align Work with your Core Purpose

First, define your freedom.

I’ve sat across from many successful people who feel completely trapped by their traditional jobs. My advice is always to stop focusing on the financial spreadsheet and start with a psychological one. The feeling of being “stuck” is rarely about money alone; true freedom comes from aligning your work with your “why.” Continue Reading…

Starting a Business to attain Findependence

Unsplash: Chris Liverani

By Devin Partida

Special to Financial Independence Hub

Many people seek the life Findependence [aka Financial Independence] can bring. While there are many ways to achieve this status, one great way is to start a business.

Building a company can be daunting, but it’s vital to consider if it’s something you really want to do.

How does starting a Business help you reach Findependence?

Many business owners trying to obtain findependence implement an exit strategy. This is where the company still operates normally but doesn’t rely on the person who started it to do the work. In other words, the company is automated to function without intervention from the owner. Other people prefer to sell their organization and live on the profit they get from it.

Instead of selling the enterprise, another route is to invest the capital in different areas. Some entrepreneurs use the profit their business generates to create additional passive-income streams.

You can invest your money in many different areas to reach findependence. Here’s a summary of a few popular avenues:

● Roth IRA: This individual retirement account [in the U.S.; similar to Canada’s TFSA] offers the investor tax-free growth and withdrawals. To withdraw money from an IRA, the owner must own the account for at least five years and exceed the age of 59 and six months.

● Property: Many entrepreneurs decide to invest their capital into real estate to sell or rent it again. Buying property could be an excellent chance to obtain passive income, which can aid with the end goal of reaching findependence. However, real estate might have additional costs, such as hiring someone to manage the investment for you.

● The stock market: You can’t talk about investing and not mention stocks. Most people are already familiar with this option, where someone purchases a portion of a company and receives shared ownership. Stocks can also generate monthly passive income via dividends, but many consider them high-risk investments.

If investing company profits to reach financial goals is something you’re interested in, there are other opportunities to look out for. Consider researching bonds and index funds to determine if they’re something you want to invest in.

What kind of Business should you start?

The type of organization you should start comes down to personal preference. Consider looking at your interests and what excites you. Many entrepreneurs create a company around what they already know. For example, if they have coding experience, they could build a business offering customers web development services. Whichever idea you choose, ensure you conduct sufficient research to know what it will take to make it a success.

Here are a few popular business ideas: Continue Reading…

Retired Money: Suddenly Retired while Covid lingers

My latest MoneySense Retired Money column looks at how the last two years of the Covid pandemic may have caused many older workers to find themselves suddenly retired, whether by their choice or not. You can find the full column by clicking on the highlighted text: Does it make sense to retire when we’re still in a pandemic?

Depending on when you had originally planned to retire — typically the traditional Retirement age in Canada is around 65 — the unexpected loss of Employment income may create any of several possibilities.

A major one is Semi-Retirement: a sort of half-way house between full employment and traditional full-stop Retirement. They may embrace a so-called Portfolio Career, generating multiple streams of income: employer pensions, government pensions, investment income, annuities, self-employment income; rental income, book royalties, speaking fees and the like.

Those in their early 60s may decide re-employment is not in the cards, which means a severance package may be your ticket to launching an encore career and becoming self-employed.

While self-employment may seem scary to those who spent more of their careers as salaried employees, self-employment doesn’t necessarily mean starting a business and employing others. Freelancing or consulting is typically a one-person gig; it may even just mean cobbling together several part-time jobs.

The column also addresses the possibility of downsizing to a smaller or less expensive place in the country, which many sudden retirees have done during the Covid era. Of course, the whole WorkfromHome phenomenon has shown how new technologies like Slack and Zoom make it possible to work remotely from anywhere with a reliable Internet connection. Two years into living with the pandemic, such technologies seem to have become permanent fixtures of working, whether remotely or a hybrid of commuting and telecommuting.

Those who were already near retirement and who enjoy good employer pensions and/or solid nest eggs from RRSPs, TFSAs and other savings, may decide they can get by without finding new employment or braving the waters of self-employment.

Time may be worth more than money

The column quotes financial marketer Darin Diehl, laid off at age 60 before Covid: “Even before Covid, my wife and I were thinking about whether we’d stay in our Mississauga home for the transition years into retirement, or downsize and relocate out of the city … Covid caused us to think about our options more thoroughly.” Continue Reading…

How to enjoy your retirement while getting paid

By Carlos Blanco

Special to the Findependence Hub

Spending a week in Napa’s wine country, enjoying the good life during retirement, and meeting new friends. Sounds like a dream, right? Having the chance to do all this and be paid might sound too good to be true, but I assure you: it’s possible!

For more than a year, I’ve been using an app called Instawork to pick up shifts whenever and wherever I want. I found the platform through a friend and began using it to pick up shifts in order to build a work schedule that best suits my personal schedule. It’s been a wonderful experience where I’ve been able to meet new people and experience different facets of the world. As a friendly guy who likes socializing, it’s been a perfect fit for me.

Prior to using Instawork, I worked as a journalist. That ranks up there as one of the most stressful careers you can have. That kind of stress can take a toll on you after a while and with me it did. The hospitality shifts I’m working now are much more relaxed and I’m truly enjoying myself. From coordinating and assisting at events throughout the year to interacting with clients and guests at a variety of different locations, no two shifts are the same. As an added bonus, I can expand my budding coaching career and attract new clients from different walks of life.

Despite Great Resignation, many still want to work

There’s a lot of talk right now in the news about the Great Resignation and the Great Reshuffle and how people don’t want to work or how the economy is dying. The pandemic shook everything up and made a lot of people reevaluate how they were living their lives and what they wanted out of work. In my view, the economy is not dying and people absolutely do want to work. They just want to do things their way, on their terms, be treated fairly, and to get paid well while doing it. The country and its hourly workers are in a period post-pandemic, where people are just transitioning from one place to another and deciding what type of jobs works best for them. Continue Reading…

Three in four Canadian Women want to start a Side Hustle

Side hustling is on the minds of a majority of Canadian women, according to a survey conducted by Angus Reid for Simplii Financial.

Fully 90% of Canadian women aged 18 to 34 are interested in exploring opportunities to earn money outside their day jobs, the survey found. And across all age groups, 76% are interested in starting a side hustle.

Most of these women are hoping to find more ways to save for major life events, including early retirement, making a down payment on a home, and growing overall savings for their futures.

This Tuesday, March 8th is International Women’s Day, and to celebrate, Simplii Financial will be hosting a special virtual event: the #SimpliiSideHustle panel [Link below.] It brings together three barrier-breaking Canadian women who have launched successful businesses, and who will offer their advice to those looking to start their own side hustles.

The panel features Canadian entrepreneurs Abby Albino (@abbyalbino on Twitter), Avery Francis (@averyfrancis), and Zehra Allibhai (@zallibhai), who will share the challenges they faced in starting their sneaker, consulting and fitness businesses, respectively. They’ll also share how they’ve challenged gender stereotypes that disempower women, to support a more equitable future.

Start-up capital a barrier for women seeking side hustles

Despite the high number of women looking to launch side hustles, more than a third of all women surveyed, and nearly half of those aged 18 to 34, indicated that lack of start-up capital was a barrier to pursuing their side hustles. Continue Reading…