By God's grace, I firmly believe I myself will be. But very often (more often than you might think), a sincere, good living brother or sister (including some you'd be surprised at) says this or writes this to me. Whatever I reply, the response is something like, " Well, OK OK, but I know I won't be there" . Doubt about salvation is that strong with them. When we feel like this, we are in some ways unreachable, we make ourselves untouchable by any spiritual reasoning- because that's how we actually want to be. So what follows probably won't help anyone in the actual moments of spiritual desperation, but perhaps these ideas can be stored away against the rainy days of future unbelief. Perhaps you are newly baptized, and find the possibility of such doubt a mystifying prospect. But all of us who've trodden the Kingdom road for any length of time can assure you that there will surely come times of spiritual crisis and spiritual self-doubt on a deeply, deeply personal level, right inside the very core of your being. Those who haven't experienced these things simply haven't grasped the awfulness of their sins, haven't examined themselves very deeply, or taken their personal responsibility and relationship to God very seriously. In this fact alone lies a challenge for the spiritually self-satisfied. The danger for those who have known the Truth a long time, or from childhood, is to never have this sense of spiritual crisis, simply because they never seriously get down to thinking about their personal relationship with God. In this case we will just drift through life, with a false sense of spiritual peace. It's what we could call the stagnant pond syndrome: the pond looks wonderfully quiet and at peace, but when you examine it you see why it's so quiet and still- because there's absolutely no life in it at all. Those who agonize that they will not be in the Kingdom certainly don't suffer from the stagnant pond syndrome; their agony of doubt about salvation is a fair reflection of their seriousness about spiritual things.
Those who " are first" in their own eyes, those who think for sure they will be in the Kingdom, will seek to enter the Kingdom at the day of judgment, but be unable. Those who strive to enter the Kingdom now are " last" in their own spiritual assessment; and the first will be made last in the sense that they won't be in the Kingdom. Thus when those who will enter the Kingdom are described as thinking of themselves as " last" , this must mean that they think of themselves now as being unworthy of the Kingdom, having great doubt about their salvation, but as " striving" to be there now, in their minds (Lk. 13:23,24). The likes of Samson died with a confession of unworthiness on their lips- in his case, that he deserved to die the death of a Philistine (Jud. 16:30)- but he will actually be in the Kingdom (Heb. 11:32). Ps. 36:8 says that God will " make us" partake of the blessings of the Kingdom of God. It reminds me of how the Lord Jesus said that in His Kingdom, He will " make us" sit down at a table, and He will come and serve us (Lk. 12:37), knowing full well that he who sits at meat is greater than he who serves (Lk. 22:27). It isn't so difficult to imagine this scene: the Lord of glory wanting us to sit down to a meal, and then He comes and serves us. He will have to " make us" sit down and let ourselves be served. Perhaps " Come, ye blessed of my Father, inherit the Kingdom" (Mt. 25:34) likewise suggests a hesitancy of the faithful to enter the Kingdom, seeing they have had such doubt about salvation. Perhaps this is typified by Joseph's revelation to his brethren; they slink away from him, and he has to encourage them: " Come near to me, I pray you" (Gen. 45:4). They absolutely knew that they ought to be punished and killed by him, and they obviously thought he would do it. Even years later, Joseph wept in frustration at their lack of full acceptance of his total forgiveness (Gen. 50:17). These scenes are so evidently typical of the future judgment seat of Joseph/Jesus.
The idea is that all those who will be in the Kingdom will feel that really we should not be there, we don't deserve it, and therefore Christ will have to almost make us go into the Kingdom. It's the same in the parables of Matthew 25, at the judgment Jesus will praise the righteous for doing so many good things, and then they will disagree with Him, they will say 'No, we didn't do that, really we didn't', and He will say 'Yes, in my eyes, you did'. It's the self-righteous, those who think they have done so much and therefore they must be in the Kingdom, who will be rejected. We must be like the man who wouldn't even lift up his eyes to Heaven but just said " God have mercy on me a sinner" - not like the Pharisee who said " I thank you that I am better than other men" . The wording of all the Lord's parables reflects His deep grounding in the Old Testament. The idea of not being able to lift up the eyes to Heaven is a common Old Testament way of expressing guilt for sin; being able to lift up one's eyes suggests a faith in forgiveness (especially in the Psalms). It could be argued that the man who wouldn't lift up his eyes to God didn't have total faith that he'd been forgiven. He just confessed his sinfulness and hoped for mercy. And yet he was the one who was accepted, for all his doubting, rather than the man who thought he could lift up his eyes to God. And the Lord designed His parables and teaching to reflect His basic knowledge that such men would characterize all who will ultimately be in the Kingdom. He spoke of us all as a little flock, fearing it is not the Father's pleasure / will to give us the Kingdom (Lk. 12:32). In doing so, He was as ever drawing on the language of the OT. Joshua-Jesus encouraged Israel that Yahweh delighted / willed that they should enter the land (Num. 14:8); but instead, they were too caught up with doubts... doubt about salvation, about what they could eat and drink day by day, and the giants in the land. This is the very context in which the Lord was speaking- fearing " the nations of the world" , doubting where food and clothes would come from, just as Israel did (Lk. 12:22-29). Yet the pleasure / will of Yahweh is that we should share His Kingdom, and that pleasure / will prospered through the cross (Is. 53:10).
I find these ideas a real challenge. We should believe that we really will, surely be saved (1); indeed, that we are already saved, in prospect, and are in embryo already the Kingdom of God. We shouldn't in that sense have any doubt about salvation. It's a terrible balance, between having faith that we will be in the Kingdom because Christ died to save us, and on the other hand having the humility, the real humility, to know we shouldn't be there. In fact, this is such an acute paradox that I would say it's one of those irreconcilable paradoxes which God has designed, and built in to our spiritual experience. Real humility doesn't come easy. It isn't remarking 'Of course, we're all sinners' in an offhand way.
It's easy to have an appearance of spiritual humility, but to cut down to the bone of the real thing is hard indeed. A warning really needs to be sounded about it. You must be able to think of examples in your own life. Here's one, a typical one, from my own; it's almost identical to a situation Dennis Gillett mentions in The Genius Of Discipleship: I once gave a series of studies to a group of brothers and sisters. A sister came up to me and told me it was the best thing she'd heard for a long time, these studies of mine had been her salvation, I was the only speaker who got through to her (etc.). I solemnly shook my head and said something like I really didn't think what I'd said was that good, and that there were lots of things I should have researched better, and that what I'd said was actually rather superficial, it didn't really get to the bone. Then I slipped away from her and went to the gents (after such a conversation), feeling I'd done the humble thing; and bumped into a brother there who I've had some differences with. He told me in that washroom that the talks I'd given were totally empty, it was a waste of time coming to hear them, and that I was misleading brethren and sisters by careless Bible study. Now all that hurt, really hurt. Yet in essence, all he said to me was what I'd said to the sister. And I realized (later!) that all I'd said to her was just surface humility. Indeed, perhaps it was worse than that: even spiritual pride dressed up as humility.
Ps. 119 reflects David's awareness that he didn't keep God's law as he should. The first four verses speak of the blessedness of the man who is obedient. But he laments: " O that my ways were directed to keep thy statutes! Then will I not be ashamed, when I have respect unto all thy commandments" (Ps. 119:5,6). He seems to be saying that when he feels he is obedient, it makes him feel ashamed because he realizes how far short he has come of obedience at other times and in other ways. He concludes this matchless psalm of praise for God's word with a seeming paradox: " I have gone astray like a lost sheep; seek thy servant; for I do not forget they commandments" v. 176). Yet often throughout the Psalm he remarks how he has kept God's law, and will thereby be justified (e.g. v.22). He expresses no doubt about salvation. The resolution of all this seems to be that we can know that we are obedient to the basic principles, and be comforted by this fact, whilst at the same time realizing how very far we come short of total obedience, and therefore how far we fall short of the spiritual blessedness which is attainable for us even now. Yet despite an agony as to his failures, David still had a remarkably open and enthusiastic relationship with God. The agony of his failures didn't take this away from him.