Let’s face it, life is crazy short and unpredictable. You could be crossing the street to your 9-5er and the unthinkable could happen. I can’t tell you how many times I have heard of people who have worked their whole lives for that moment to retire from the job they hate to pass away unexpectedly once they retire – never really being able to enjoy the retirement they had worked so tirelessly for. With the way in which you are able to make a living these days, there is NO excuse to stop what you hate doing and start doing what you love. Whether you are just starting your career or nearing the end of your traditional ‘work life’, career pivots are possible as long as you take the right steps. Career pivots require self awareness, networking, accountability, honesty and an action plan.

Going from a pension and benefits to freelance can be a frightening thing. From worrying where your next pay check will come from to having to pay out of pocket for health benefits, it can seem overwhelming but it IS possible. Personally, I have made this jump a few times in my life. It seems that any time I get comfortable, I instinctually look for change.

From film a day guy to time-lapse guy to corporate guy to married guy

I started out working for the Ministry of Education in Canada doing video work with pension and benefits. With this job, I didn’t feel fulfilled so transitioned to a full-time freelancer. While freelancing, I realized there was a gap in the local market so I started a video production company. At the same time, I dug pretty heavily into time-lapse photography and started to mainly get time-lapse jobs. To break from this, I started to focus on stories that pushed me creatively that didn’t revolve around time-lapse shooting. I pushed pretty hard in the commercial world and managed to land some good clients. Again, feeling like my creativity was becoming stagnant, I ended up taking a bit of a step back from this. In all of the scenarios leading up to this point, the pivots happened very strategically. However, jump cut to meeting my wife and all that careful planning was thrown out the window. I ended up getting married and relocating to San Francisco.

My current career pivot is the scariest of the lot as I have no experience with the market or industry here. This was the first time where I didn’t have a clear picture of my path. However, times like these can sometimes be the best as some things become clearer much faster when your hand is forced. For me, this transition has really helped me hone in on what I enjoy doing and what I am good at. This forced period of transition really allowed me to find clarity. Thinking deeper about it, I guess you can say that change is normal for me whether it is forced or not.


There are challenges that come with making a career pivot whether forced or planned. For me, it is more of a psychological war more than anything. When making a change like this, you are leaving the comfort of your current environment for a path of uncertainty. If you are making the jump to that of a freelancer, you are taking on an even bigger challenge. To ensure success, there are a few things you can do.

1. Baby Steps First – Finding Fulfillment

Don’t take action without a plan. If you are considering a career pivot, think of the transition in baby steps. The video above shows one way where you are able to build the path you want rather than following the path that is set out for you.

When considering a drastic shift in how you spend your time, considered what brings you fulfillment. If you can’t find fulfillment in your current job, where do you current find fulfillment? What does this life you dream of look like?

2. Self Awareness

Before you can even consider making a change, you need to be aware of where you are most happy and what brings you the most happiness. If it is as simple as work-life balance or the desire to spend more time with your family or friends, what would allow you to achieve this? What type of work would you need to do that would allow you to achieve this? Does your current scenario allow for this as an option?

Having a clear idea of what you like and don’t like is the first step to ensure you are working towards a life you desire. Spend some serious time mapping out what you enjoy about your life and what you could use less of. Mapping out your priorities is a great way to start to design your life.

To achieve any change, you also need to take accountability. Accountability forces you to be honest with yourself and the more harsh you are, the closer you will get to the truth.

3. Building a Network / Relationship Building

Any transition needs a strong network. From a personal support system to collaborators and clients, it is key that you have a network to build upon. Relationship building on all three levels is the best investment you can make. Regarding the personal support system, that keeps you going through the tough times and is also a potential channel for lead generation through their extended network. Collaborators are also important to keep your creativity flowing as well as a potential channel for work and or talent to hire for your jobs. Lastly, when it comes to clients, my rule of thumb is to have three clients at any given time. The biggest reason for this is to ensure that if you loose one source of income, you are able to still pay the bills for the most part. Clients are always coming and going (unless you are able to lock in the long term clients with for some people is the ultimate goal) so it is key that you don’t put all your eggs in one basket.

4. Short and Long Term Goals

Before you make a career change, you have to understand what you want, both in the short and long-term. Think of this as your five and / or ten year plans. This is where you need to get real with yourself as to what is important in your life. If you want a work / life balance and are currently feeling like you are working too much, think about what a balanced lifestyle will give you. What is it about that balanced lifestyle that is so important for you? Maybe your goal is to produce your first feature film. If so, what will having produced a feature bring for you? What is it specifically about producing a feature film that motivates you? Knowing not only what you hope to achieve in your life but also the ‘why’ will ensure that your motivations are pure. Keep in mind that this may evolve over time which is totally okay. The key is to at least be striving towards something with the right intentions (and careful planning so that if something happens unexpectedly, you are able to react in a well-informed / educated manner that continues to drive you in the right direction towards these larger goals).

5. Build an Action Plan / Critical Path

Action plans are actionable items that contribute towards a goal. It is basically a list of tasks that need to be achieved, in order for the goals to be reached. Action plans are an important part of strategic planning for any change, but unfortunately many people tend to stop after the strategic plans have been laid out. Without having a way to achieve these goals, the initial planning that went into the first stages towards a career pivot may be for nothing. Think of it like making a new years resolution. You may state that you plan on losing weight or that you want to be more creative. However, it is impossible to act on these things without a detailed plan or intention. Same thing goes with career pivots.

Now once you have a clear idea of the next actionable steps, you will then want to blue print out a critical path. This will lay out the framework as to how things need to roll out in order to implement the pivot. Don’t get overwhelmed at this stage – this is simply a step that ensures you have your butt covered. This also helps when creating the jump off point – that is, the point in which you feel comfortable to make the final transition.

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