The seeds of what became LiveWorkPlay were planted in the early 1990s. Co-founders Keenan Wellar and Julie Kingstone both shared a passion for helping young people enjoy a better quality of life, and were alarmed at the lack of effective services for people with mild and moderate intellectual disabilities.

After years of exploring these issues with parents, teachers, and other concerned individuals, in 1995 they decided to develop an organization that they hoped would one day make a difference.

After incorporating the organization and receiving charitable status in 1995, they dedicated two years to building a strategic plan and pursuing startup funding. After working closely with the Ontario Trillium Foundation for more than a year, four years of startup support began in the spring of 1997. Julie and Keenan left their existing careers and started the work of building LiveWorkPlay.

In the winter of 1998, the fledgling organization added new board members, recruited volunteers, and launched its first programs, which initially were offered on evenings and weekends.

The Network 303 programs served different age groups starting at 13, and offered opportunities to develop life skills in community-based settings. The program was an immediate success, and led to the development of a summer learning program, which was also launched in 1998.

In 1999, LiveWorkPlay began the first year of a two year partnership with Human Resources Development Canada in hosting a Youth Services Canada initiative to explore workplace issues for people with intellectual disabilities. These projects were of a critical nature, as they led to the identification of key issues in supporting young adults to live as included and contributing members of society. These findings drove the creation of Skills and More for Independent Living and Employment (SMILE), an individualized system of supports for adults making the transition to a fuller life in the community.

The SMILE system of supports was proving very effective, and after applying through a public request for proposals process, was chosen by MCSS to receive ongoing funding in partial support of its operation. After some five years of continuous fundraising and strategic planning challenged by financial unknowns, the organization was enabled to increasingly turn its focus to further improvement of its quality programs.

In the summer of 2001, LiveWorkPlay joined with five other charitable organizations and moved into the previously abandoned building at 153 Chapel Street.

In the fall of 2002, the organization began taking a serious look at housing issues, a logical extension of the SMILE system of supports in promoting greater independence for people with intellectual disabilities. Interest in the self-advocacy movement also began to grow at this time.

In 2003 and again in 2004, LiveWorkPlay conducted housing projects based out of a student residence at Carleton University. The projects of 30 and 50 days (with 10 and 14 participants respectively) resulted in the conclusion that proximal living with peers in a non-institutional setting was a model with many benefits.

In 2004-2005 as part of  a Policy Governance process the Executive Staff and Board of Directors developed a new mission statement that was approved by 95% of the membership at the 2005 Annual General Meeting. The mission speaks to the organization's intended outcomes (ends) rather than methods (means). Whereas the means may change frequently, the ends are the constant measuring stick by which the organization can determine its progress.

People with intellectual disabilities will progress as self-advocates and contributing citizens while the organization ensures a high level of financial and moral accountability, transparency, and efficiency.

At the organization's annual Visioning Day in June 2006 many parents revealed that they were "burnt out" with trying to take the next step in supporting their adult children to move out of the family home. In September 2006 LiveWorkPlay hosted a conference event to target this issue and continued working with interested families on developing concrete plans and timelines to "make it happen."

In December 2006 LiveWorkPlay announced its formal housing strategy, whereby families would be encouraged to purchase outright or partner with other families to own a home where their adult children would live. In recognition of the reality that a purchase option was out of reach for some, LiveWorkPlay engaged in a capital fundraising campaign and purchased two condominium units which are rented affordably to four adults with intellectual disabilities. Within the next year another 7 individuals moved into a home of their own.

In September 2007 LiveWorkPlay launched the On Our Own Together Too transitional housing program. This initiative is being funded by the Community Foundation of Ottawa for three years.

OOOT-TOO offers two months of supported independent living to adults with intellectual disabilities who are interested in practicing living with a roommate in an apartment setting. Professional support staff help participants and families establish goals for OOOT-TOO.  A report is provided at the project conclusion to help participants see where they stand in terms of realizing their own housing goals. In some cases OOOT-TOO is a direct "launch pad" for moving on to a more permanent housing solution.

In May 2008 the LiveWorkPlay organization became an Affiliate of Community Living Ontario. LiveWorkPlay applied for membership mainly out of interest in working with like-minded people and organizations to better educate the public about people with intellectual disabilities, their needs, and their abilities.

In 2009 a key challenge for LiveWorkPlay is to figure out how to work with  funding sources that are tied to systems that have difficulty accommodating the LiveWorkPlay approach. LiveWorkPlay supports and services are highly individualized, seek to respond rapidly to changing needs, and often involve the coordination of paid and unpaid contributors to individual support networks. This "non-program" approach stretches the boundaries of the developmental services system, and at times challenges LiveWorkPlay to choose between what is right and what is most convenient to the system. It may seem obvious that the needs of the person should always come first, but if this comes at the expense of a loss of funding that will make it impossible to provide any supports at all, then the choice becomes very difficult indeed.

While dealing with these challenges in the present, LiveWorkPlay is actively working to contribute to future systems transformation through participation in various bodies that bring together service agencies and government. 

Over the course of 2009-2010, LiveWorkPlay made significant moves in transitioning from a social services model to a facilitator of social capital and social change. Day programs were eliminated, and resources were increasingly targeted to helping our members find and keep paid employment, find and keep affordable housing in the community, and develop meaningful relationships with people who are not paid to spend time with them.

In keeping with this evolution, LiveWorkPlay moved to the C3 Centre in September 2010. The C3 Centre is a unique collaboration of capacity-building organizations sharing space at 1155 Lola Street, Suite 201.