As he began his farewell tour Monday with a press conference at the state Capitol, U.S. Sen. Joseph Lieberman reflected on his quarter century in public office and how much things have changed.

Back in February 1988, when Lieberman announced his candidacy for the U.S. Senate, “a blackberry was a fruit and tweeting was something birds do.”

“Google and Facebook were words without meaning,” Lieberman said. “But we sure know now what they mean.”

It was the popularity of blogs and the beginnings of social networks that may have contributed to Lieberman losing the Democratic primary to Ned Lamont back in 2006. However, the driving issue during that campaign was the War in Iraq. It was Lieberman’s position on the war that created a deep divide between him and his party.

For the past six years the Democratic Party in the state hasn’t really known what to do with Lieberman, even though some have remained deeply loyal.

Asked to described Lieberman, Gov. Dannel P. Malloy, said he was “someone you could frequently agree with, but you weren’t always going to agree with.”

Lieberman, the first Jewish-American vice presidential candidate in 2000, won re-election to the Senate in 2006 as an Independent and was at that point still tolerated by the Democratic Party.  Two years later in 2008, when he endorsed Republican U.S. Sen. John McCain’s presidential candidacy at the Republican National Convention, Connecticut Democrats decided enough was enough.

Lieberman’s picture disappeared from the wall of Democratic headquarters in Hartford, but the party fell short of censuring Connecticut’s then-junior Senator. Instead, they decided to send him a strongly worded letter to let him know they disapproved.

Connecticut Democratic Party Chairwoman Nancy DiNardo said she was disappointed in Lieberman for going to the Republican National Convention.

“Joe Lieberman has many taken many earlier positions — prior to 2008 — that were supportive of the Democratic party,” DiNardo said Monday in a phone interview.

In Washington, the Democratic establishment was more forgiving and allowed Lieberman to retain his chairmanship on the Homeland Security and Governmental Affairs Committee.

In 2009, when it came to a vote over the Affordable Care Act, Lieberman declined to support a final version if it included a government-run public option. He even went so far as to say he would join the Republicans in blocking debate on the bill. The position put him at odds with his friend and former colleague U.S. Sen. Chris Dodd, who retired back in 2010.

Eventually, Lieberman reached an understanding with Democratic leadership and the health care bill was passed without a public option.

But those are just some of the legislative and political battles over the past six years. Lieberman was a state Senator before becoming attorney general and before spending four terms in the U.S. Senate.

So what’s next? Lieberman retires on Jan. 3 and has been told by former colleagues that it would be a mistake to make any decisions too soon.

“Part of why I left the Senate now is because I feel good and I wanted to leave at a time, not when I could totally retire, but have another chapter in my professional life,” Lieberman said.

He said his home in Washington is for sale and he’s moving back to Stamford.

As he makes his way back to the Nutmeg state he will be doing a farewell diner tour to thank as many people in Connecticut as he can for giving him an opportunity to serve. His tour started Monday at Shady Glen Restaurant in Manchester.

When he makes his valedictory speech on the Senate floor this week, he said he won’t talk about the things he felt he was able to accomplish during his tenure. Instead, he said he will “really try to draw some lessons from my 24 years in the Senate. Particularly to those who remain in the Senate, what I hope that they will focus on, and the types of changes that they’ll make.”

He said the U.S. Senate has really become “dysfunctional and unproductive.”

“Because of partisanship. A lot of it is because of ideological rigidity and the inability to compromise,” Lieberman said.

Unlike Dodd, who used his farewell speech in 2010 to talk about why the Senate needs to maintain its rules and traditions, Lieberman said he thinks the Senate needs to change the filibuster rules.

“The requirement that you need 60 votes to proceed to a matter, to consider an amendment, to pass a bill finally, to take up a conference report, all of those require not 51 votes, the majority, but 60,” Lieberman said.

The thought behind the filibuster rule was “by requiring a supermajority you stop an irrational passion,” Lieberman said. “I haven’t seen too many passions, irrational or otherwise, sweep through Congress into law because of the inherent checks and balances in the system the constitution created.”

“The filibuster is not constitutional,” Lieberman said. “It’s a matter of the Senate rules.”

“If I had my druthers I would run the Senate just the way the House is run,” Lieberman said.

He said if he had any disappointments over the past 24 years in the Senate, it would be that he never got the 60 votes necessary to move forward with bipartisan legislation to address global warming and climate change.

“We did get over 50 once and it should have passed then, but it didn’t because of the 60-vote requirement,” he said.

His second disappointment is not being able to get a cybersecurity bill passed.

“We’re vulnerable to a cyber attack that will be more devastating than 9/11 was,” Lieberman said. “It will be an attack on our critical infrastructure that’s privately owned.”

He said they got over 50 votes to take up the legislation this past summer, but it wasn’t enough.

According to this New York Times story, McCain, one of Lieberman’s closest allies in the Senate, led the opposition to the legislation. 

“There’s two big things where I think our country is really threatened,” Lieberman said of climate change and cybersecurity.

While his future is still unknown, Lieberman ruled out lobbying and announced his intention to use his leftover campaign funds to start a scholarship program for Connecticut residents seeking to attend a Connecticut four- or two-year school.

Lieberman’s scholarship fund, which he hopes to have up and running by next year, will reward up to five students with $1,500. He said he hopes the awards will help the students leverage more money to cover the cost of their educations.

Lieberman said he won’t be the one deciding who gets the scholarships, but plans to handle the fundraising.