Image source: TransCanada Corporation.

TransCanada (TRP 0.59%) has certainly faced its share of challenges over the past few years. This is the company that spent six years trying to get the Keystone XL oil pipeline project approved only to face such intense opposition that it was eventually rejected. While it wasn't able to overcome that challenge, it hopes to have success in overcoming a number of additional challenges it's facing right now.

No. 1: Overcoming opposition to Energy East
When progress stalled on the southbound Keystone XL pipeline, TransCanada turned its attention to the east by proposing to build the Energy East pipeline. The project would convert a vast swath of underutilized natural gas pipeline for oil services to move oil from the country's western oil sands region to refineries and an oil export terminal along the country's eastern coast.

That project, however, has run into its own share of road blocks. Heavy natural gas users in the eastern part of the country are concerned that by converting natural gas pipelines to oil service, they will see higher prices for gas. They are voicing their opposition to the project, which is putting it in jeopardy. Convincing the opposition and government regulators that the project is in the country's best interest is a big challenge that TransCanada needs to overcome.

No. 2: Finding the cash it needs to fund its recent acquisition
With Keystone XL rejected and major opposition to Energy East, TransCanada has turned to acquisitions to drive growth, recently announcing that it would acquire U.S. based Columbia Pipeline Group (NYSE: CPGX). It was an all-cash deal valuing Columbia Pipeline group at $13 billion, including the assumption of debt. In going the all-cash route, TransCanada has had to seek outside funding for the deal.

To date, it has secured $4.21 billion via a brought deal offering, which is a good start. However, it's still several billion dollars short, which could be a problem given that capital markets have started to close their doors to energy companies in recent months. Because of that, the company is exploring a range of options to fund the deal, including exploring asset sales. According to reports, the company is working with banks to sell upwards of $7.1 billion in assets, including its power assets and a minority stake in its Mexican natural gas pipeline business.

That said, the timing for asset sales might not be right given the currently weak market conditions. In fact, analysts think the company, which paid $2.9 billion for some of its power assets in 2008, might only be able to fetch $1.98 billion for them today. Suffice it to say, finding the cash to fund this deal in the current market environment is a big challenge.

No. 3: Overcoming obstacles in the west
In 2012, TransCanada was selected by Royal Dutch Shell (RDS.A) (RDS.B) and its partners to develop a multibillion-dollar natural gas pipeline to Canada's West Coast. The Coastal GasLink project was expected to cost $4 billion and link gas from the Montney region to Shell's proposed LNG export facility near Kitimat B.C. called LNG Canada. A year later, it was selected by another LNG project to develop a $6 billion natural gas infrastructure project. That project included the $5 billion Prince Rupert Gas Transmission project, which would also bring gas from the Montney region to the West Coast to serve the Pacific NorthWest LNG project near Price Rupert, B.C.

However, amid sagging support and slumping commodity prices, Shell recently pressed pause on its $50 billion LNG Canada project. Likewise, Pacific NorthWest LNG continues to face delays, which has pushed back that project's timeline. Given these delays and current commodity prices, it's possible neither project will be built for quite some time, if at all. That puts TransCanada's multibillion-dollar western expansion projects in jeopardy, which is another big challenge for the company to overcome.

Investor takeaway
TransCanada is facing a number of big challenges, which have the potential to derail its growth. That said, the company has been knocked down by challenges before, only to get back up and move in a different direction. It will need to continue to either overcome challenges, or quickly change course in order to deliver the robust dividend growth its investors are expecting to see over the long term.