When you look at career paths, you might think they are linear, but in reality, they can take many turns.

(PHOTO CREDIT: Demetri Martin, “This is a Book“)

This drawing fittingly explains the reality of what career success will look like for many of us in the new age of employment. It is well-known that we have moved from the days of one career to having multiple careers in our lifetime – and this applies to all industries and sectors. 

I recently had a conversation with someone who has worked with hundreds of executives in the charitable, government and social profit sectors. She was adamant that the successful leaders of the future will not be the ones with the most knowledge, the most skills or the most experience, but with the strongest ability to adapt and change. This requires gathering a variety of skill sets and perspectives – the type you can gain from shifting career paths.

In that case, experiencing multiple careers is not a bad thing – it can actually work in your favour and prepare you for the employment landscape of the future. 

After 8 years working at an internationally known charity, being provided opportunities to advance into new roles, and ending up in the helm of the fundraising department, overseeing a team of 8 people and raising over $8M annually - I decided to take on the role of Executive Director of a much smaller (or as I prefer to say, small and mighty) organization.

How to decide if a move like this is right for you?

My current seat is within an organization that I volunteered with intensely for eight years before joining as the Executive Director. I felt deeply invested their success before starting. While this move was a difficult choice because I felt very much fulfilled and connected to my last shop; the decision to move ultimately came down to a matter of following my gut and asking some key questions to engage my brain:

• Can I be the lead champion for this cause? Can I demonstrate boundless passion and share the vision to draw others in?
• What skills, knowledge, perspectives and new connections do I stand to gain by making this move?
• What risks am I taking by leaving my past role and stepping into something very different?
• Where are the current knowledge and skills gaps, and in what areas would I need to learn and grow immediately?
• Who are the current staff I will be working with? Is the right team in place to achieve success or are significant changes needed?
• What is the culture of the Board of Directors? What type of relationship are they looking for with the Executive Director?
• What supports do I have to guide me through this journey?

Asking yourself questions like this will serve as a self-interview, making sure you are listening to your heart and your head in the right quantities.

What is the difference between heading up fundraising at a large organization and leading the charge at a smaller organization? 

If you are considering such a move, there are some important differences between large and small organizations, and between lead fundraising roles versus lead management roles, which you should be aware of. The following tips may help you prevent total culture shock when you make the leap:

• There is a huge learning curve around administration – payroll, HR, finance, governance, marketing and communications - think of it as running a small business. All bucks stop with you and you wear more hats than LL Cool J. There is no director of marketing or vice president of human resources – it all comes down to you.
• Small organizations require tremendous entrepreneurial spirit, lightning fast decision making, and the ability to take risks on a regular basis. It’s not that these don’t exist in larger organizations, because they certainly do, but often they can conflict or become lost within larger structures.
• There is a much less established fundraising program. The base of donors, average gift and largest gift are much smaller, and there are less fundraising channels and tools embedded within the organization. There are likely two to three pillars such as a key campaign, funder or event. What this does mean is you have the chance to work from a clean slate and build great new programs with no existing structures to break down – sometimes that can be easier.
• You are now reporting to a Board of Directors instead of a CEO. This requires a different approach to reporting, relationship management and governance. Working with a Board of Directors means you have a large in-house pool of talent, wisdom and mentorship to draw support from, and this also means there are more people you need to keep aware, informed and engaged with your work on a regular basis.
• Working long, hard hours…no wait, that isn’t any different!

Strategies to shifting into an Executive Director role?

Here are four key things I learned making the shift to being an Executive Director:

1. Seek advice and mentorship from those that have done this before or who are leading organizations successfully – in this sector, there are many generous and wise leaders who want to see you succeed. Ask and you will be surprised who says yes to being a support for you.
2. Establish your presence right away with all your stakeholders. Spend a lot of time up front listening, engaging and making yourself known. As the face of the organization, it is critical that key donors, funders, volunteers and partners begin to get to know you and trust you, as you will be working together.
3. Don’t try and fix problems that you don’t understand. Talk to the people – they often have the answers – or at least can clarify the issues.
4. Be very conscious that what you did to be successful so far is not the same as what you will need to be successful going forward. Old habits may need to change. Rethink and unlearn.

Making a career shift can be scary, but can stretch your perspective, challenge you to build new skills and be a wonderful stage in your journey. There is no one right way to do things – it depends on your personal definitions of success. Wherever you go, bring your best self, develop positive reputation and stay in touch with the people who matter – that is always important. Besides, this decision is never final – you can always go back the other way, now armed with some new skills and a broader lens that you bring with you.

Rickesh passionately believes that every donor deserves to feel excellent about giving, and that the duty of a fundraiser is to bring passion towards enhancing the donor experience every day. He is adamant about always putting people first, then process, and that fundraisers, charities and social profit groups should not be afraid to have a personality. Rickesh is the Executive Director at Future Possibilities for Kids, where they provide leadership and life skills development programs for children and youth from underserved communities. Prior to this, Rickesh was the Director, Campaign at United Way York Region, leading an $8M annual fundraising campaign. He is on the Board of Directors for the Association for Fundraising Professionals of Greater Toronto and is the lead organizer of Be Good Be Social York Region, a conference promoting social media for social good.