Career Goals: Side Hustle Your Way Into Independence


(Image credit: Getty Images via @daylife)

An athlete needs good hustle. Your successful side hustle needs good hustle, too, whether it’s intended to earn extra money, achieve secondary career goals, or transition into a main gig for greater independence.

When Pete and I decided to embark on our Plan “B” career goals, we set up several side hustles. Our previous work experience hadn’t really prepared us for what we needed to do to earn extra money. But we did plan for lots of dedicated activity: good hustle which we intended would eventually transition our work into a location-independent lifestyle. While Pete continued work as Director of Marketing for a wildlife non-profit and I worked in my gift basket business, we added considerable good hustle with freelance consulting work, online stores, blogging, and a travel-based business opportunity. These were ambitious plans, and we knew the only way our team of two would succeed with these new career goals was with focus and determination.

Launching a side hustle is easier than sustaining one.  Working on what is essentially a second job with few initial rewards and no guarantees are not the sort of career goals many of us have been conditioned to make. Yet, good hustle encompasses this reverse conditioning which conventional wisdom warns against. There’s very little payoff when you begin any sort of entrepreneurial endeavor, and there’s always the chance there won’t be any later. Many well-meaning naysayers will continually bring up this risk. Good hustle in your side hustle requires you ignore them.

Hustle (TV series)

Hustle (TV series) (Photo credit: Wikipedia)

Here’s how you put good hustle into your side hustle:

Objective #1: Visualize. Your side hustle can be a tool that helps you accomplish location independence, more passive or residual income, or even early retirement. Go into it with a positive outlook and be open to opportunities and possibilities.

Objective #2: “Keep your eyes on the prize.” Just as an athlete will practice and drill on a daily basis, you’ll need to keep daily priorities in alignment. Make sure you’re spending time appropriately. Consider a daily quota for yourself so you can measure your output. Good hustle depends upon commitment, as well as extreme focus.

Objective #3: Prioritize and strategize. You do this by evaluating your current circumstances vs. where you want to be. For example, if you want to quit your job, how long will it take to achieve the necessary level of side hustle income for you to afford it? Can you realign your expenses in order to accomplish it sooner? Keeping a strategic focus will levitate your side hustle from just a way to earn extra money into a long-range vehicle that supports your overall goals.

Cover of "Escape from Cubicle Nation: Fro...

Sustaining your side hustle is imperative if you’re ever going to achieve an Escape from Cubicle Nation. Pamela Slim, who wrote this call-to-arms, knows that “more substantial businesses can and do emerge from side hustles.” Those that consistently earn extra money are the ones must achieve sufficient momentum to make the break. But many people are unprepared for the time and effort this takes.

We took several years to transition our side hustles into complete work-life integration. We began this blog, for example, in 2008. Not long after, we started our group of online stores. When they began to earn extra money, we got excited, and this motivated us to keep working. Our other activities have taken longer to come to fruition.

Even with the best intentions, converting a side hustle into a reliable earning machine can be a daunting proposition. We’ve seen many people talk about getting started only to make a very short-term effort. They kick the tires and take a test drive, but they don’t take the car home much less drive it for a several months or a few years.

Even a short period of time with disappointing results can seem like a reason  to quit. But this rarely a get rich quick proposition. Be in it for the long haul. Dedicating a specific amount of your time each day or week to your side hustle, resisting the temptations of distraction or procrastination, keeping a positive attitude, and evaluating and adjusting your cumulative results will lead you where you want to be.

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  1. says

    Hi Betsy .. it does take time, courage, and courage of our convictions to know things will pan out .. and taking new ideas and opportunities if appropriate, and adjusting those in, as time continues on its way … you’ve both done amazing jobs to get where you are along the path of freedom – sustaining it too .. you’re good examples to us all .. cheers Hilary
    Hilary has an awesome blog post here: C is for Croft Castle – a Welsh Border Castle in HerefordshireMy Profile